Affordable Accommodations Near Chincoteague Island, VA

Channel Bass Inn and Restaurant
Bed & Breakfast
6228 Church Street, Chincoteague, VA, VA 23336

Channel Bass Inn and Restaurant in Chincoteague provides accommodations with free bikes, a garden, and a shared lounge. The air-conditioned accommodations are 13 miles from Mid-Atlantic Regional Spaceport. The bed and breakfast provides a restaurant serving American cuisine, as well as free Wifi throughout the property. The bed and breakfast offers a seating area with a flat-screen TV and a private bathroom with bathrobes, a hair dryer, and shower. At the bed and breakfast, all units include bed linen and towels. Guests at Channel Bass Inn and Restaurant can enjoy an American breakfast. The bed and breakfast has a picnic area where you can spend the day outdoors. Salisbury-Ocean City Wicomico Regional Airport is 48 miles away.

Guest Reviews:

- "Wonderful" - "A place to stay like no other" - "Fantastic stay, left rejuvenated and happy!" - "Nice getaway in a romantic setting."

Blufin Bungalows & Marina
House
2477 Main St, Chincoteague, VA, 23336, USA

While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a full-sized refrigerator/freezer, as well as a stovetop and free WiFi. Other amenities include towels, kitchenware and utensils, a toaster, and a sitting area.

Guest Reviews:

- "Awesome time" - "My kids (13 and 7) spent a long weekend in one of the floating bungalow boats. We had a blast! The bungalow was super clean and cute. The views from our bungalow and our property were gorgeous. The pool overlooking the water was a hit also. We will likely come to stay again. Such a fun and unique experience." - "Great place we will be back next year" - "It was a weekend trip for me and my daughters. It was everything we needed. Very clean, comfortable and very good location. I highly recommend this place. The only thing is towels. I would have liked to have had them replaced but it was my fault for forgetting to ask. My only complaint is more lighting in the back parking lot. It was very hard to see when walking down the ramp. I am guessing the lack of light is due to bugs though so I understand that. "

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
House
5386 Main Street, Chincoteague, VA, 23336, USA

Offering a garden, Cottage w Private Creek, Sunroom, Fire Pit, & WiFi offers accommodations in Chincoteague. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Cottage w Private Creek, Sunroom, Fire Pit, & WiFi features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Salisbury-Ocean City Wicomico Regional Airport is 50 miles from the property.

Guest Reviews:

- "I'll be back" - "Great stay" - "It was enjoyable." - "clean, spacious , relaxing area"

Chincoteague Apartment w/Deck: Walk to Waterfront
Apartment
6294 Cropper St, Chincoteague, VA, 23336-2420, USA

Located in Chincoteague, this welcoming apartment brings it all within your reach. Robert N. Reed Downtown Waterfront Park is just steps away and Chincoteague Channel is within an easy 14-minute walk, so leave your car at the property, which offers onsite parking.

This 1-bedroom, 1-bathroom rental features a living room, a BBQ grill, air conditioning, and a ceiling fan. Enjoy the free WiFi and TV. The kitchen is equipped with a microwave, cookware, and paper towels. And you can even travel light because you'll have a washing machine. Other amenities include bed sheets, a desk, and heating.

Amenities:

Security/Safety • Other • Tv • Ocean View • Bedding/Linens • Oceanfront • Fireplace/Heating • Laundry • Kitchen • View • Internet • Air Conditioner

Chincoteague Townhome with Pony Views from Deck!
House
Chincoteague, VA, USA

Guests staying at this vacation home have access to a balcony. Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 15 miles away. The air-conditioned vacation home is composed of 2 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. A flat-screen TV and a DVD player are provided. For added privacy, the accommodation features a private entrance. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Guest Reviews:

- "Relaxing and fun girls trip."

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
House
Chincoteague, Virginia, USA

Your Chincoteague adventure begins at this 2-bedroom townhome. Step inside and be greeted by the gorgeous decor and soothing ambiance. The living room, with its beautiful furnishings, offers a cozy space to relax after a day of exploring. Rest easy in the king bed or queen bed in the bedrooms, each designed for your comfort. With 3 bathrooms, you'll have plenty of space to freshen up before heading out to discover the quaint fishing village with the horses that made this beautiful land across the water famous. We've thought of everything to make your stay enjoyable, from WiFi to a washing machine. We'll be available to answer any questions during your stay!

Guest Reviews:

- "We recently had the pleasure of staying at an incredible townhome, and we can't recommend it highly enough! From the moment we arrived, we felt the warmth and hospitality that truly made us feel at home.The space was beautifully decorated, impeccably clean, and equipped with every amenity we needed. The attention to detail was impressive—from the plush bedding to the well-stocked kitchen, which made our stay not just comfortable but also enjoyable, and we can't recommend it highly enough! From the moment we arrived, we felt the warmth and hospitality that truly made us feel welcomed.The space itself was beautifully decorated, impeccably clean, and equipped with every amenity you could need. The attention to detail was impressive—from the plush bedding to the well-stocked kitchen, which made our stay not just comfortable, but also enjoyable. The hosts went above and beyond to ensure we had everything we needed, and were readily available for any questions.One of the highlights of our stay was the serenity we felt. The location was also perfect; it was just a short distance to local attractions, restaurants, and parks.We also appreciated the thoughtful touches. It truly felt like a home away from home.Overall, our experience at this townhome exceeded all expectations. If you're looking for a cozy, inviting place to stay with exceptional hosts, book this property immediately. We can't wait to return!"

Beach Bay Pony Place with Ponies 1 Mi to Water!
House
Chincoteague, VA, USA

Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 13 miles away. The air-conditioned vacation home consists of 2 bedrooms, 2 living rooms, a fully equipped kitchen with kitchenware, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are provided in the vacation home. The accommodation has a fireplace. Salisbury-Ocean City Wicomico Regional Airport is 49 miles away.

Amenities:

Internet • Parking • Child Friendly • Guest Services • Fireplace/Heating • Accessibility • Other • Security/Safety • Sports/Activities

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
House
Chincoteague, Virginia, USA

Ask me about seasonal weekly & monthly discounts!
Stay comfortably in Chincoteague at this 2-bedroom house, just a short 5 minute drive to the beach. 🏖🌞 Nestled in a perfect coastal town, this relaxing retreat offers an escape for guests. With 2 queen beds, you'll find restful nights and wake up refreshed to explore the wonders of Chincoteague. The house boasts modern amenities like a washing machine, AC, heating, iron, WiFi, and a hair dryer. The 3 bathrooms ensure convenience, and the living room with a sofa bed provides additional space for relaxation.

Enjoy a relaxing experience at your vacation home situated just steps away from Maddox Blvd. Providing easy access to shopping, dining and the beach road. This beautifully renovated home features luxury vinyl plank flooring, bright kitchen, white cabinets, & granite counter tops and a tiled backsplash.

Immerse yourself in the beauty of this charming destination and create unforgettable memories. We look forward to hosting you at our place.

Smart lock with personalized check-in code, code will be provided prior to check-in.

We are available via Direct Message for any questions during your stay. We are committed to making your stay a pleasant experience.

Longer term stays welcome, great week long and month long stay discounts.

Internet/Wifi:
Lightning fast internet provided; Work can’t wait while you are on your weekend getaway or extended stay? We got you covered!
3 Smart TVs with the ability to log into streaming services, one in each bedroom plus the living room.

Furry Family Members: 🐕
We keep the treat jar stocked for our furry guests in the entry area on the cabinet! You will not be able to miss it! There are food & water bowls provided as well. Ran out of waste bags? No worries! We have you covered and have plenty of waste bags to use! Simply toss the used waste bag in the outdoor garbage container. If you go out and about to explore and unable to bring your furry family member, we have a large dog crate provided in the laundry room area. There is a $10 per night pet fee per dog up to 2 dogs, owner permission required prior to stay.

Walk to the places in Chincoteague!
- Island Creamery- 0.5 miles
- Pico Taqueria - 0.25 miles
- AJs on the Creek - 0.4 miles
- Teaguer's Pub - 500 feet
- Ledo Pizza - 200 yards
- YMCA - 0.3 miles
- Mister Whippy coffee & ice cream - 0.6 miles
- Captain Zack's Seafood - 0.4 miles
- Surfside Golf - 0.3 miles
- Funland Amusements - 0.25 miles

Guest Reviews:

- "This place was amazing. The decor was perfect for the island and the house had everything we could have needed. The host was very responsive with communication and check in was super easy. We will definately stay here again when we come back. " - "This was exactly what we needed. The property is delightful with everything you could need. It was clean and very comfortable. The hosts stayed in touch with us and were available if needed. We are looking forward to returning soon!"

Horseshoe Haven
Apartment
7111 Horseshoe Drive, Chincoteague, VA, VA 23336, USA

Horseshoe Haven is a recently renovated apartment in Chincoteague where guests can make the most of its outdoor swimming pool, free bikes, and garden. Among the facilities of this property are a restaurant, hairdresser's, and beauty services. There's a sun terrace and guests can use free Wifi and free private parking. Featuring a patio and pool views, the spacious apartment includes 3 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 2 bathrooms with a walk-in shower. The comfortable, air-conditioned accommodation also comes with soundproofing and a fireplace. The property has an outdoor dining area. There is an on-site coffee shop. You can play table tennis and tennis at the apartment, and the area is popular for snorkeling and cycling. The apartment also comes with outdoor fireplace and a picnic area for a day outdoors. Mid-Atlantic Regional Spaceport is 14 miles from Horseshoe Haven. Salisbury-Ocean City Wicomico Regional Airport is 50 miles from the property.

Amenities:

Restaurant • View • Oceanfront • Security/Safety • Barbecue/Outdoor Cooking • Guest Services • Balcony/Terrace • Pet Friendly • Pool • Accessibility • Internet • Sports/Activities

3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room
House
Chincoteague, Virginia, USA

Close to the beach! Enjoy this unique and tranquil 2 bedroom home with occupancy for 6. Pack and play crib is also available.
Bottom floor also has a double futon, game/tv/fitness room! Private big back yard to grill and have bon fires. Three spacious decks! 2 decks with a water view and enjoy feeding deer off the back deck.

Guest Reviews:

- "An awesome place. A piece of paradise for sure. Host went above and beyond to make us feel right at home. Definately plan on going back again" - "This was a quick family getaway and the house was clean and comfortable. There was a heatwave with extreme heat index (102). We didn’t get to do all of the outdoor activities we wanted and the house and pool table/game room saved the day. We were so comfortable we didn’t even want to go out to dinner (we did and AJ’s on the creek did not disappoint). The homeowner was very responsive to messages and the location was a peaceful retreat but a quick drive to downtown ). "

Key West Cottages
Villa
4251 Main Street, Chincoteague, VA, VA 23336

Key West Cottages offers air-conditioned rooms in Chincoteague. This beachfront property offers access to a balcony, tennis at the tennis court, free private parking, and free Wifi. The villa provides an outdoor fireplace and a 24-hour front desk. The villa provides guests with a terrace, a seating area, cable flat-screen TV, a fully equipped kitchen with an oven and a microwave, and a private bathroom with shower and a hair dryer. A fridge, a stovetop, and kitchenware are also provided, as well as a coffee machine. At the villa complex, every unit has bed linen and towels. There is a snack bar, and a mini-market is also available. Sightseeing tours are available nearby. Cycling, fishing, and hiking are possible within the area, and Key West Cottages offers a private beach area. Mid-Atlantic Regional Spaceport is 12 miles from the accommodation. Salisbury-Ocean City Wicomico Regional Airport is 48 miles away.

Guest Reviews:

- "The place is so beautiful. We enjoyed it so much. Definitely will come back." - "It was wonderful and definitely plan to return back . The property management was terrific." - "Perfection!" - "The property was beautifully landscaped and well cared for." - "Da Best Trip Ever" - "Susan was great! Very friendly staff." - "Absolute perfection, nothing could be improved" - "Great place, Art was very helpful!" - "Outstanding property. Very close to everything. Very nice cottages and the pool is awesome."

Josie's Getaway - Pet Friendly -Mini-Vacations and Month to Monthly Available
House
Chincoteague, Virginia, USA

Mini-Vacations and Monthly Rental Available. Amenities: New Queen Mattress, Recushioned sofa and new deck furniture for 2025 season Central A/C, Dishwasher, Microwave, New full-size W/D, 2 TVs, Smart TV and Roku, Wi-Fi, Charcoal Grill, Screened Porch, Outside Shower.Linens and towels provided. 2 dog maximum.

Perfect pet friendly beach getaway located right off Ridge Rd close to restaurants and shopping. This quaint cottage offers all the amenities, with bright, open rooms, perfect for a comfortable vacation. This house has a large, screened porch, outside shower and fire pit on the patio. Been working hard over the cold months to make Josie's Getaway as perfect as ever. We listen to your comments and are always looking to improve our cottage. For 2025 we have New Queen Mattress, Recushioned sofa and new deck furniture. Linens and towels provided.

Pet friendly home $75. (per pet) will be added to your reservation. 2 dog maximum. only. 2 night minimum in off Season.

Cancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days:the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).

Bed Sizes: 1 Queen, 2 Twins, 1 Queen Sleep Sofa

Sunday Change Over

2026 Off Season $ 137 per night / $ 954 for week
2026 Prime Season $ 193 per night / $1351 for week
2026 Pony Swim Week $ 1652 per week ( 7 day minimum)

**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ***
***Month to Month availability***

Guest Reviews:

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Another Chincoteaque holiday at Josies... maybe my third year... Always love coming here, suits my needs perfectly!" - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We love Josie’s Getaway. We appreciate the gift basket the owner gives us each visit. It so special, I really believe she goes above and beyond in picking out each item for our family. Our grandkids really appreciate the items she puts in there for them and so do our dogs. This house is so cute. We love staying at Josies. We look forward to each vacation on this special island. Maybe one day we will be lucky enough to call this home."

Blufin Bungalows & Marina
House
2477 Main Street, Chincoteague, VA, VA 23336, USA

Blufin Bungalows & Marina offers accommodations in Chincoteague, 15 miles from Mid-Atlantic Regional Spaceport. There's a private entrance at the vacation home for the convenience of those who stay. The vacation home also offers facilities for disabled guests. Accommodation is equipped with air conditioning, a fully equipped kitchen with a dining area, a flat-screen TV, and a private bathroom with a bath or shower. Free Wifi is accessible to all guests, while certain rooms are equipped with a patio. At the vacation home, each unit includes bed linen and towels. Guests at the vacation home can take part in activities like yoga and get refreshed with a swim in the outdoor swimming pool. Fishing is possible within the area and Blufin Bungalows & Marina offers a private beach area. Salisbury-Ocean City Wicomico Regional Airport is 51 miles from the property.

Guest Reviews:

- "Josh was awesome...made our trip experience wonderful!" - "Great place to stay - great view!" - "It was so refreshing" - "We really enjoyed and will be back🌞🌞" - "Overall loved our stay." - "Good new vacation spot, but a few upgrades could"

Your Memorable Island Vacation Starts Where the Sidewalk Ends!
House
Chincoteague, Virginia, USA

Sidewalk's End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evenings spent strolling, shopping, playing miniature golf, exploring the many restaurants, and of course the ice cream parlors. The Comfortable living room with plenty of seating, is the perfect place to unwind and relax while watching TV. The kitchen is furnished with stove, refrigerator, microwave, pots and pans, dishes, crock pot, glasses, utensils and much more. This home also offers a Spacious Master Bedroom with 1/2 bath, 2nd bedroom with 2 twin beds and a full bath. The Large back yard is the perfect spot for family picnics, and gatherings, and you will even find a picnic table, and outdoor shower. Your Memorable Island Vacation starts where the Sidewalk Ends! This home has a NO SMOKING and NO PETS policy. We ask that you bring your own sheets (2 Queen, 2 Twin), and towels. A washer and dryer is provided for your convenience. Please leave the home in a neat and tidy condition.

Guest Reviews:

- "Property was nice. In great location, easy access to everything. House was clean and fitted our needs." - "Where the Sidewalk Ends is a beautiful home just off of the Main Street (Maddox Blvd) in Chincoteague. The home is larger inside than expected. The kitchen was fully stocked with knives, kitchen gadgets and has counterspace needed to prepare meals. We walked to all of the shops and Ice Cream places daily. A small Dollar General is also in walking distance which came in handy for things we forgot. We were able to enjoy the first night of the Fireman's Carnival on our last night here. Thank you for making our stay memorable."

Chincoteague Bay RV Resort & Cottages
House
2272 Main Street, Chincoteague, VA, VA 23336, USA

Chincoteague Bay RV Resort & Cottages offers accommodations in Chincoteague, 15 miles from Mid-Atlantic Regional Spaceport. Private parking is available on site. The vacation home offers sea views, an outdoor fireplace, and free Wifi is available throughout the property. All units comprise a seating area with a sofa, a dining area, and a fully equipped kitchen with various cooking facilities, including a microwave, a toaster, a fridge, and a stovetop. All rooms are complete with a private bathroom and air conditioning, and some rooms also offer a balcony. At the vacation home, the units have bed linen and towels. Guests may eat at the on-site family-friendly restaurant, which is open for dinner. For guests with children, the vacation home features outdoor play equipment. Guests can swim in the infinity pool or go fishing. Salisbury-Ocean City Wicomico Regional Airport is 51 miles from the property.

Guest Reviews:

- "Beautiful place, clean, friendly people and service." - "Memorable!" - "Amazing time, great location, wonderful staff!" - "Outstanding" - "Mini Vac 5/22/24" - "We enjoyed it immensely. Assatauge beach within 10 min drive where one can view the wild horses." - "Vacation of a lifetime" - "an amazing experience" - "Amazing." - "The perfect weekend get away. Already booked a week in 2025. The perfect place to relax and unwind!"

Hancock House -Single Family Home - Screened Porch, NO LINENS PROVIDED
House
Chincoteague, Virginia, USA

Amenities: Central A/C, Dishwasher, Microwave, W/D, TV, Cable, Outside Shower, Screened Porch, Open Porch, WiFi, Electric Grill

This historic island home is immaculate! Tucked away on a private lane with a large, screened porch overlooking a lovely yard. A perfect spot to unwind and enjoy your beach vacation! Remodeled kitchen and bath, new laundry room, spacious living room and open front porch with distant views of Oyster Bay.

NO LINENS AND TOWELS ARE PROVIDED SO BRING YOUR OWN OR CALL US TO RENT THEM.

Cancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less, then 30 days:the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge, and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).

Bed Sizes: 1 Queen, 1 Double, 1 Twin

Saturday Change Over

2026 Prime Season Rates $ 1225 per week
2026 Off Season Rates $ 875 per week / $ 125 per night 3-night min.

**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Guest Reviews:

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderfully restored duck carver’s home. The home was charming, clean, great location, and had a well loved feel to it. We had a wonderful time there during pony penning week." - "Check in was very easy.House was clean and tastefully decorated.Located on quiet street but still close to amenities and attractions."

Chincoteague Island Cottage about 2 Mi to Beaches
House
Chincoteague, VA, USA

Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 12 miles away. The air-conditioned vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a shower and free toiletries. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Salisbury-Ocean City Wicomico Regional Airport is 48 miles from the property.

Guest Reviews:

- "We had a great time exploring Chickadee, this house was in the perfect location for everything we wanted to do" - "Perfect location in a quaint cottage setting" - "We had a cozy, quiet getaway with lots of nature walks and ice cream right across the street. My kids are already asking" - "Cute cottage. Plan on eating out."

An Unfettered View - Beautiful ranch w/boat dock!
House
Chincoteague Island, Virginia, USA

This beautiful 2 bedroom ranch home has a quiet, out-of-the-way location situated on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck. It's perfect for crabbing, kayaking & canoeing! An Unfettered View features all amenities including a private master suite with full bath, central air, all appliances including dishwasher, washer/dryer, wireless internet service and a wonderful family room on the waterside of the home. Tastefully furnished and very accommodating, this is a great vacation spot! An Unfettered View is wheelchair accessible.

​​​​​​​- No smoking is permitted on the premises.
- Linens and towels are included with your reservation.
- No pets are permitted on the premises.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Guest Reviews:

- "Even with the wind and rain we had a great time." - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My sister and I stayed for a long weekend in the Unfettered View beach house. It was beautifully decorated and clean. Just lovely! We had a great time and didn't have to worry about a thing. Thank you!"

Quaint Chincoteague Island Hideaway with 2 Porches!
House
Birch Town, VA, USA

Providing a spa and wellness center, Quaint Chincoteague Island Hideaway with 2 Porches! offers accommodations in Birch Town. Guests staying at this vacation home have access to a patio. Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 14 miles away. With direct access to a balcony, the air-conditioned vacation home consists of 3 bedrooms. Offering a terrace, this vacation home also has a cable flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a shower and a hair dryer. The property has an outdoor dining area. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Guest Reviews:

- "Amazing private family getaway 10 minutes from the ocean."

Cypress Cottage -Waterview-TOWN LINENS AND TOWELS/Beach Supplies Provided
House
Chincoteague, Virginia, USA

Cypress Cottage is a vacationer’s delight. It combines the rustic nature of historic Chincoteague with an extensive list of amenities rarely found in most rental properties today. Whether staying for a week or just a long weekend, the features included with this cottage make planning and packing for your stay as carefree as the stay itself. Please look over our amenities list and see all of the things you will not have to bring, buy or rent to make your stay special. Bikes, beach chairs and all of your linens are just a few of the great list of items we provide at Cypress Cottage.

Amenities: 2 bedrooms with queen beds, 1 bathroom with tub/shower, Full eat-in kitchen w/table that seats 6, Living room w/65” TV w/sofa and 2 armchairs, Bonus room w/double futon and 39” TV, Fenced yard, Air conditioned, Bay view, Washer & Dryer, All linens provided, sheets, blankets, pillows and towels, including beach towels, 2 Throw blankets, Propane gas grill w/cooking utensils and pans, Exterior dining table with 6 chairs, 2 adult Trek bikes with 2 helmets. 1 junior bike, Bike rack, pump, 4 beach chairs, 62 qt cooler, Beach umbrella, 12’x12’ beach canopy tent, 2 boogie boards, Beach dolly, Corn hole game, Assorted games and books, K-cup/12 cup pot coffee maker, Toaster, Air fryer, Blender, Hand mixer, Can opener, Slow cooker, Hair dryer, Extensive cookware, bakeware and bowls, Dinnerware for 8, Silverware for 8, Glassware, wine glasses (both glass and plastic), Rubbermaid food storage containers, Trash bags, Extensive kitchen utensils, Aluminum foil, plastic wrap, Basic spices, Salt & pepper, PAM, Hand soap, dish soap and room deodorizer sponges, dish towels, paper towels and toilet paper, Kleenex, napkins and paper bathroom cups, First Aid kit, Flashlights, Fire extinguisher, High speed internet, Smart TVs with Built-in Fire sticks. Free streaming for Netflix, Amazon, Disney+, HBOMax, PBS+, Fox Nation, and Paramount+. No cable, Iron and ironing board, Propane fire pit w/exterior seating, Exterior storage shed and Outside Shower for when you return from the beach.

(Disposable supplies limited to on hand quantities at start of stay. Any replenishment during stay is the responsibility of the tenant. On hand quantities should be sufficient for a week’s stay.)

Cypress Cottage is a vacationer’s delight. It combines the rustic nature of historic Chincoteague with an extensive list of amenities rarely found in most rental properties today. Whether staying for a week or just a long weekend, the features included with this cottage make planning and packing for your stay as carefree as the stay itself. Please look over our amenities list and see all of the things you will not have to bring, buy or rent to make your stay special. Bikes, beach chairs and all of your linens are just a few of the great list of items we provide at Cypress Cottage.

Cancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days:the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).

Bed Sizes: 2 Queens, 1 Double Futon

LINENS AND SHEETS PROVIDED

Saturday Change Over

2026 Prime Season Rate $ 1309 weekly
2026 Pony Swim Rates $ 1410 weekly
2026 Off Season Rates $ 806 weekly / $ 160 per night

**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Guest Reviews:

- "Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The cottage was very cute and well equipped with everything you could think of. It’s perfect for families with kids. The beds are comfortable, the room adjacent to the living room is perfect to play board games with the kids. The outdoor shower is a dream with soap and shampoo dispensers and additional towels. Beach towels and chairs are provided. 2 adult bikes and one medium size are also available. Don’t expect much storage place in the kitchen because it’s already fully equipped. We had to store our pantry items outside the kitchen. I would definitely go back!"

3 Mi to Beach Waterfront Condo in Chincoteague!
Apartment
Chincoteague, VA, USA

Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 14 miles away. The air-conditioned apartment is composed of 2 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are featured in the apartment. For added privacy, the accommodation features a private entrance. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Pet Friendly • Other • Security/Safety • Fireplace/Heating • Child Friendly • Guest Services • Parking • Internet

Island Escape: Bikes, Kayaks, Grill, Firepit, Beach Gear, Large Quiet Property
House
Chincoteague Island, Virginia, USA

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you!

If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

-- Update! We now have horses right in front of the house! Note: They are not always there.

-- Large detached garage with kayaks (life jackets not provided), charcoal grill, bikes, boogie boards, beach chairs, and other beach items.

-- Pony Swim goers! You can walk to the Pony Swim from our house in just a few minutes. Plenty of parking as well. Most of the time, the saltwater cowboys with the Reed family walk right through our front yard!

Our home is the perfect getaway for those looking to escape the hustle and bustle of the city and enjoy a peaceful vacation. The house is located in a quiet residential area, with easy access to the beach and other attractions.

The house features 2 bedrooms, 1 bathroom, and a spacious living area that is perfect for entertaining that also offers a queen bed. The kitchen is fully equipped with all the necessary appliances and cooking utensils for you to whip up delicious meals during your stay.

This house has been in our family since it was built in the 1940s. The house was smaller back then but had an addition put on sometime later. We bought the house from the family a few years ago and have been renovating it a little at a time. We have put a lot of work (and heart) into keeping the charm of the house while trying to update it with some conveniences. With all of this being said, we hope you are comfortable and enjoy the house as much as we do.

Step outside and you'll find a beautiful backyard with a barbecue grill and plenty of seating for you to enjoy the fresh air and sunshine. In the evenings, gather around the fire pit for some s'mores and stargazing.

You will see plenty of deer, geese, and ducks on the property at any given time. The porch is an amazing place to sit at the end of the day with a cold drink and watch the sunset. If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

Chincoteague Island is known for its stunning beaches, wildlife refuge, and historic lighthouse. Take a stroll along the beach, go fishing, or enjoy a boat tour to see the famous wild ponies.

We are confident that you will love staying at our house and exploring all that Chincoteague Island has to offer. Book your stay today and get ready for a relaxing and unforgettable vacation!

You will have access to the entire home and large property for grilling and chilling!

I am available by phone or email if you need anything during your stay.

Guest Reviews:

- "Accommodations were outstanding, comfortable and cozy! Even provided lots of sunshine! A great short vacation." - "My family of 4 had a wonderful stay at this house. I would recommend this house and come back. The owner is very responsive." - "At the time I booked this property, there were only 2 reviews, and I was hesitant to stay without knowing more. But the description and the pictures looked great, so we decided to give it a chance. The home was exactly as described, though the family room and kitchen areas were even bigger than we imagined. There was a lot of beach-themed decor, which added to the charm. We had some questions for the owner, including during our stay, and he always replied immediately. It was about a 10 minute drive to the beach, but regardless of where you stay on Chincoteague, you'll have to drive to the beach. It was very close to Memorial Park, which had a nice playground for younger kiddos, and is where they do the Pony Swim. It was close enough to the main street with a majority of the restaurants. We would definitely recommend this property and stay again."

Chincoteague Apartment with Deck Walk to Waterfront
Apartment
Chincoteague, VA, USA

Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 13 miles away. The air-conditioned apartment consists of 1 bedroom, a living room, a fully equipped kitchen with a microwave and a coffee machine, and 1 bathroom with a shower and a hair dryer. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Salisbury-Ocean City Wicomico Regional Airport is 48 miles away.

Amenities:

Internet • Fireplace/Heating • Security/Safety • Accessibility • Child Friendly • Guest Services • Other • Parking

CoZyQ is a 2-bedroom, 2 full baths cottage in charming Chincoteague Island, VA
House
Chincoteague, Virginia, USA

Located on the quaint Chincoteague Island, our charming 2 bedroom/2 full bath CoZyQ home is nestled on a quiet road with a relaxing view of a small horse farm from the back screened porch. With a queen bed, 2 XL Twin beds, and 2 full size futons, CoZyQ comfortably accommodates 6 people…a portable crib and highchair are also provided. Restaurants, shopping, tennis courts, Memorial Park, and the fairgrounds are an easy walk or bike ride away. The Maui Jack’s Water Park and the entrance to Assateague Island National Park are approximately 1.5 - 2 miles away, and the beach is 3 miles away. CoZyQ offers all the necessities needed for a stress free and relaxing visit. No need to haul in bottled water…CoZyQ has a whole house water softener system and a water and ice reverse osmosis system at the refrigerator and kitchen sink. The kitchen is furnished with a plentiful assortment of kitchen essentials and a gas stove to satisfy the desires of the family chef. Both a Keurig and drip coffee makers, toaster oven, microwave, dishes, pots and pans, blender, slow cooker, flatware, spices, and other cooking accessories are available. Three TV’s with Roku guest devices and a DVD/Blu-ray player, high speed internet, movies, puzzles, games, and books for various age groups provide entertainment for relaxing evenings. Wall mounted hair dryers, washer and dryer, ironing board/iron, bed linens, bath towels, beach towels, beach chairs, umbrellas, boogie boards, coolers, ice packs, a beach wagon, a gas grill and an outdoor shower are provided for your convenience. Additionally, 2 air purifiers and introductory bath/dish/laundry soap, paper towels, and toilet paper are provided. EV charging station (40 amp) is available. We are confident that CoZyQ will meet your comfort, cleanliness, and convenience standards for an enjoyable visit to Chincoteague Island.

Guest Reviews:

- "Beautiful property, perfect location, hosts were incredible. Accommodations were perfect, our family has been coming to chincoteague for years and cozy Q was by far our favorite. Book with them and you won’t be disappointed!!! " - "Lovely, fully-stocked cottage in a great neighborhood. Very quiet yet centrally located. We biked to almost everything. Lots of good storage, hooks and shelves. Beautiful furnishings, all comfortable. Large porch and outside shower. We wanted for nothing! We hope to return sometime and highly recommend!"

Chincoteague Charm Escape with Bikes and Yard Games!
House
Deep Hole, VA, USA

Both parking on-site and free Wifi are available at Chincoteague Charm Escape with Bikes and Yard Games!. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a shower and free toiletries. A flat-screen TV with cable channels, game console, and DVD player, as well as an iPod docking station are provided. The property has an outdoor dining area. Salisbury-Ocean City Wicomico Regional Airport is 49 miles away.

Amenities:

Other • Internet • Ocean View • Sports/Activities • View • Accessibility • Pet Friendly • Oceanfront • Fireplace/Heating • Security/Safety • Parking • Guest Services

Oyster Bay Hideaway on Chincoteague Island!
House
Chincoteague Island, Virginia, USA

Oyster Bay Hideaway - Beach Days are the Best Days…..

Just imagine relaxing on the Deck taking in that salty, sweet bay breeze - listening to the Tree Frogs sing - and watching Herons, Eagles, and Egrets fish for their morning meal in Eel Creek just behind the house…..

This is living the shore life at Oyster Bay Hideaway on beautiful Chincoteague Island. In the perfect mid-Island location, this adorable Townhome truly has it all - great views, the comfort and amenities you want and need, and you can bring your family dog! After all, it’s only a Family Vacation if the whole family gets to come!

Oyster Bay Hideaway is tucked away on Teal Lane, just off of Maddox Boulevard, aka the Beach Road, which will take you to heavenly Assateague National Seashore. You can walk to many Shops, Restaurants, and even Amusements, such as Mini Golf, Go Carts, and more. While being awesomely close to everywhere you want to be, Teal Lane is a very quiet street with no outlet, and the home is all the way in the back - nice and quiet, and away from the busy road. Yet hop in your car, and you’re at the Beach in just a few minutes!

You will love the layout of Oyster Bay Hideaway - just perfect for a small family or 2 couples traveling together. After a fun-filled day exploring Assateague or searching for our famous Wild Ponies, kick back in the comfy Living Area and stream your favorite flicks on the Flat Screen TV (Streaming Only), or simply take in the gorgeous Views behind the house. Adorned in Beachy Blues, with floors reminiscent of a stroll on the Boardwalk and Exposed Wood Beams, it has that perfect beach house feel. Step out onto the Back Deck and be WOWED by the gorgeous Views of Eel Creek, which leads to Oyster Bay. There is a Shared Pier for fishing and crabbing, or just stargazing - but there is no road, and no homes directly behind you - just lovely views, peace, and serenity.

The Chef in your family will love the spacious Eat-in Kitchen - everything you need for a quick
bite before exploring the Island, or a more leisurely dinner. Don’t feel like cooking? Stroll to Maria’s, Ledo’s, Pico Taqueria, The Village, or Famous Pizza - all within walking distance!

Oyster Bay Hideaway sleeps 5 more than comfortably with 2 Master Bedrooms, each with its own Private Master Bath. Bedroom 1 is bright and cheerful with sunny yellows and a comfy Queen Bed and Flat Screen TV. Bedroom 2 is decorated with colors of Sea Glass - blues, grays, and pale greens - just lovely. Both Full Baths have a Tub/Shower Combo.

Affordable and Adorable, Oyster Bay Hideaway is the perfect home base for all of you Chincoteague Island Adventures. Book your time on our Little Island by the Sea today!

One well-trained dog is welcome with a $100 Pet Fee. Must be current on Vaccinations, and Flea & Tick Preventative. Accidental Damage Waiver does not cover Pet Damage.

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.

Guest Reviews:

- "It was great!" - "It was great." - "3rd visit to the Island- and it’s become our New Favorite- check in and host communication was easy and very pleasant- we’ll be back next year!" - "Parking and check-in were very easy, with clear directions provided by the agent. The home was clean and nicely appointed, exactly as shown in the listing. The beds and other furnishings were comfortable, and the kitchen had plenty of dishes, flatware, and pans. The only small downside was that when outside on the deck we could hear the loud music from the nearby mini-golf, which went quite late into the night. Still, the home is very nice and it was a pleasant stay."

2 Mi to Downtown Tranquil Abode in Chincoteague!
House
Chincoteague, VA, USA

Providing a garden, 2 Mi to Downtown Tranquil Abode in Chincoteague! provides accommodations in Chincoteague. Both parking on-site and free Wifi are available at the vacation home. The air-conditioned vacation home consists of 3 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Parking • Fireplace/Heating • View • Pet Friendly • Security/Safety • Other • Internet • Ocean View • Guest Services • Accessibility • Sports/Activities • Oceanfront

‘Beach Bay Pony Place’ w/Ponies: 1 Mi to Water!
House
Chincoteague, Virginia, USA

Escape to coastal paradise with this charming vacation rental in Chincoteague Island, VA. Spend your getaway with our Chincoteague Ponies — or bring your own! Offering a barn with stalls and a horse pasture with a run-in, this spacious 2-bedroom, 2-bath home is the perfect retreat for avid riders. Witness a sunset on the beach, explore Chincoteague National Wildlife Refuge and Assateague Island, or simply cozy up by the fireplace. Don't miss out on this gem for your visit to the Eastern Shore!

-- THE PROPERTY --

Horse-Friendly Property |
Bedroom 1: King Bed | Bedroom 2: Queen Bed | Sunroom: Sleeper Sofa | Living Room: Sleeper Sofa

INDOOR LIVING: Smart TV, board games, books, fireplace, group-friendly dining table, sunroom
OUTDOOR LIVING: 2 12x12 horse stalls w/ pasture, front porch w/ outdoor seating, garage game room w/ ping pong table
KITCHEN: Cooking basics, Keurig coffee maker, dishwasher, stove/oven, refrigerator, microwave, kettle, toaster, knife block, dishware & flatware
GENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, in-unit washer & dryer, laundry detergent, central heating & air conditioning, iron/board, hair dryer, trash bags & paper towels
FAQ: Optional horse-boarding fee (paid pre-trip), 3 exterior security cameras (facing out)
ACCESSIBILITY: Stairs required for access, single-story home
PARKING: Driveway (2 vehicles), horse trailer parking available

-- THE LOCATION --

BEACHES + PARKS: Toms Cove Park (2 miles), Assateague Island National Seashore (3 miles), Chincoteague Beach (3 miles), Chincoteague National Wildlife Refuge (4 miles)
ISLAND EXCLUSIVES: Chincoteague Island Farmers and Artisans Market (1 mile), Captain Timothy Hill House (2 miles), Museum of Chincoteague Island (2 miles), Assateague Lighthouse (4 miles), NASA’s Wallops Flight Facility Visitor Center (6 miles)
HIKING + BIKING TRAILS: Island Nature Trail (2 miles), Bivalve Trail (5 miles), Woodland Trailhead (5 miles)
OFFSHORE EXCURSIONS: Captain Dan’s Around the Island Tours (0.8 miles), Daisey’s Island Cruises (0.9 miles), Barnacle Bill’s Wild Pony Boat Tours (3 miles)
FISHING SPOTS + CHARTERS: Downtown Chincoteague Waterfront Park (0.8 miles), Captain Steve’s Bait and Tackle (2 miles), Captain Bob’s Marina (2 miles), Island Queen Inland Charters (3 miles)
AIRPORTS: Salisbury Regional Airport (48 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: Your safety matters. This property features 3 exterior security cameras. The 2 cameras on the outside of the home are not activated and do not record video or audio. There is a camera in the barn facing the horse stalls and pasture for horse safety. This camera actively records video and will be turned on during your stay
- NOTE: This single-story home requires a small set of stairs to access
- NOTE: Optional horse boarding is available for an additional fee paid on-site to the Guest Contact, whose information will be provided after your reservation is complete & paid in full

Guest Reviews:

- "The house is spacious, beautifully decorated, clean, and very comfortable. Residential setting makes it quiet and easy access to shopping, restaurants, grocery store, gas, harbor, beach, scenery and the wild horses ! Horses on the property are icing on the cake !! I was blessed to start and end my days visiting Trigger, Crystal and Surf.Owner/host is such a lovely person, very accommodating, a local resident, very knowledgeable about the island, a passionate horse lover, and is very easy to work with. Our stay was a fabulous combination of adventures, great seafood, and relaxation. She is also a realtor and would be my choice to find our own place on the island."

Chincoteague
House
6360 Pine Dr, Chincoteague, VA, VA 23336, USA

This property offers access to a terrace, free private parking, and free Wifi. The spacious vacation home is composed of 3 bedrooms, a living room, a fully equipped kitchen, and 2 bathrooms. A flat-screen TV with streaming services is available. The accommodation is non-smoking. Guests at Chincoteague will be able to enjoy activities in and around Chincoteague, like cycling. Salisbury-Ocean City Wicomico Regional Airport is 50 miles from the property.

Amenities:

Guest Services • Internet • View • Parking • Other • Bar • Balcony/Terrace • Oceanfront • Security/Safety • Ocean View • Air Conditioner • Sports/Activities

Riptide’s Crossing: A waterfront getaway w/deep water dock and incredible views
House
Chincoteague, Virginia, USA

When you need to check off ALL of the boxes, you'll find everything you’re looking for at "Riptide's Retreat".

Named after one of Chincoteague's most beloved wild ponies Riptide, we've got everything you need to enjoy a spectacular vacation filled with memories that will last a lifetime.

Every morning you can enjoy a peaceful sunrise as you look out towards the beautiful refuge where you'll find the southern heard of the famous Chincoteague Ponies. You'll also have direct views of the Assateague Lighthouse and Little Beach where you can paddle over and enjoy a more private beach experience.

We provide all the essentials PLUS bikes, kayaks, beach/fishing cart, Bogg beach bags, beach towels, crab pots/traps, and more.

Come and enjoy the most amazing views from our multiple decks that look out over the Chincoteague Channel and the southern end of Assateague Island. You'll have unobstructed views of the Assateague Lighthouse as well as Little Beach both just a short kayak paddle away. There's plenty of parking for you and your guests too.

Want to bring your boat? We've got you covered. You'll have access to our BRAND NEW private DEEP water footing dock. Want to enjoy fresh crab for dinner? Use our crab traps and enjoy the freshest seafood ever.

We've even included an outdoor dining area with seating for 10. You'll have a propane grill for your favorite feasts and there's a great spot with a firepit so you can make all the smore's you want for dessert.

If you're wondering where the famous pony swim takes place each July, it shouldn't surprise you that it takes place on PONY SWIM LANE. You'll have a FRONT ROW SEAT when you stay at Riptide's Retreat during that magical week in July. Literally there is NO OTHER vacation rental on the entire island of Chincoteague that will get you closer to the wild ponies on swim day.

But the BEST PART OF Riptide's Retreat is that you don't have to be there during Pony Penning week in July to see the ponies because they roam year round as they graze in their natural environment just across the channel on the Chincoteague National Wildlife Refuge. If you want an up-close personal experience, you can paddle over with our kayaks or jump in your boat for a super quick ride.

By the way, the reason our home is called "Riptide's Retreat" is that Riptide is one of the most recognizable ponies in the southern herd and we're confident that you will likely see him and his band of beautiful mares during your stay. His dark chestnut coat contrasted by his beautiful blond mane makes him the "Fabio" of all ponies. I'll bet you will spot him during your visit.

As the owners of four vacation rentals on Chincoteague Island, this one packs the most punch and definitely has that WOW factor for guests as they arrive and gaze out at the water and Assateague Island.

We can't wait to see you come and enjoy.

Our home is pet friendly. Inquire with the host regarding limitations. This is a Sunday to Sunday rental during the peak season June - Mid September

Guest Reviews:

- "We stayed 3nights here and it was wonderful. The host is very generous with allowing access kayaks and bicycles so there was plenty to do outdoors. The house is well equipped with appliances and dishes, and it has two beautiful porches to sip your coffee and look at the ponies across bay. We can’t wait to return to this peaceful oasis!! " - "The location is perfect! Lots of extras like the kayaks and bikes. We wish we could have stayed the whole week. We would definitely stay again!"

Jellystone Park Chincoteague Island
House
6742 Maddox Boulevard, Chincoteague, VA, VA 23336, USA

Jellystone Park Chincoteague Island offers accommodations in Chincoteague, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home provides an outdoor swimming pool and an ATM. A mini-market is available at the vacation home. For guests with children, Jellystone Park Chincoteague Island offers outdoor play equipment. A water park and an indoor play area are available for guests at the accommodation. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Guest Reviews:

- "We will be back!" - "We had a nice stay the two nights we were there." - "Relaxing and family time was amazing"

Sunset Villa
Villa
Chincoteague, Virginia, USA

THE REEF VACATION VILLAS INCLUDE THE FOLLOWING FOR OUR GUESTS:
*All units sleep 6
*Daily and Weekly Rentals Available
*Full Kitchen
*Use of Inclusive Indoor Pool
*Free Wifi
*4 FREE Maui Jack Waterpark passes (Seasonal)
*Free Bike Rentals
*On-Site Grills and picnic area
*Free Parking
We are located just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse. This 2 Bedroom, 1.5 Bath Villa sleeps 6 and features a full kitchen with pots, pans, utensils, dishes and drinkware, toaster, coffee pot, microwave, refrigerator/freezer and oven. To make your trip to paradise even easier, we've included bed and bath linens, toilet paper, paper towels, trash bags and dish soap. Your Villa provides 2 parking spaces.

Complimentary washers & dryers are located on property. Heated indoor pool is open April thru November.
Close to the Beach...... Close to PERFECT!

Guest Reviews:

- "My family and I were very pleased with our stay. The location was easy walking distance to the Assateague bridge and many food trucks/restaurants, yet was very quiet in the later hours. Our kids loved the indoor pool and the extras offered. We are already planning a repeat stay!" - "Fun family time!" - "Property was clean and tidy. Communication with the owners was great. Super kind and friendly. Traveled with my spouse and 2yo daughter. My family enjoyed the pool multiple times a day. Enjoyed grilling on location with accessible grills. Our villa was perfect for our needs. Water park across the way was included and a hit with my kiddo. Have already recommended to friends and family for a getaway vacation even with kids. Would recommend to anyone looking for an friendly enjoyable stay "

Beach House @ The Reef
House
7023 Maddox Boulevard, Chincoteague, VA, VA 23336, USA

Beach House @ The Reef offers accommodations in Chincoteague, 14 miles from Mid-Atlantic Regional Spaceport. This property offers a private pool, free Wifi, and free private parking. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 1 bathroom. A flat-screen TV is provided. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 49 miles away.

Amenities:

Security/Safety • Child Friendly • Internet • Parking • Air Conditioner • Pool

Pelican Sunset - Waterfront With Pier
House
Chincoteague, Virginia, USA

Pelican Sunset is a waterfront cottage on the Chincoteague channel. Enjoy beautiful sunsets, kayaking, and fishing from the dock. The house is clean, comfortable, relaxing, updated & decorated with original art from Hawaii, the Caribbean, and the Eastern Shore.

The property is 4 miles from Assateague National Seashore Park and ½ block from where the Annual Assateague Pony round-up parades horses to the carnival grounds. The dock is also located in view of the NASA Wallops Island launch site.

Please note: There are video cameras on the property which monitor the driveway, the dock, and the rear street entrance of the property lot. There are no cameras within the house.

Please note: Pelican Sunset now offers the property with sheets and bath towels included for guests use.

The space:
Pelican Sunset has a dock for launching your kayak/canoe, fishing, crabbing, clamming, and sun bathing which extends into the Chincoteague Channel. There is a private deck outside the master bedroom which overlooks the southern Chincoteague channel. The enclosed front porch faces the waterfront/dock and the Chincoteague channel where fishing boats regularly come and go. There are two large screen wall mounted televisions, one in the downstairs den, and the other in the master bedroom. There is also a smaller television in the guest bedroom. The house is equipped with WiFi and television service for the main TV provided through a ROKU streaming device, a Blue Ray, and an antenna. The other two televisions have Blue Ray and antenna TV. Bedrooms are located on the second level and accessed by a spiral staircase. The master bedroom holds a king size bed, the guest bedroom holds a 54" double bed and 48" double bed. The downstairs den holds a queen sleeper sofa. The full bathroom, and half bathroom are located on the downstairs level. In addition, an outdoor shower is also available which is private, located behind the house, and is accessed by a brick walkway. The Pelican Sunset kitchen is renovated with a beautiful granite countertop and stainless steel sink, and fully stocked with pots and pans for cooking. The kitchen also is equipped with a gas range and oven, microwave, blender, juicer, toaster, and drip coffee maker. Because all island septic systems have limited capacity, Pelican Sunset provides a small washer and dryer for light laundry needs. The house has central Air Conditioning for guests comfort.

Come explore the Island, relax and enjoy the fantastic sunsets at Pelican Sunset!

Guest Reviews:

- "We arrived to fresh fruit and vegetables on the table. The house is located in a perfect spot for a quick drive to the beach. But you can also sit on the dock for an amazing sunset. House was clean and very inviting. We will be back next year. Thank you Tom" - "We had such a great stay at Tom’s place. He was very responsive and communicative which was very nice. The house was super clean and we loved fishing on the dock. We’d definitely stay here again!"

Gone Coastal - Pet friendly with screened porch!
House
4410 Eastwinds, Birch Town, VA, 23336, USA

Gone Coastal - Pet friendly with screened porch! offers accommodations in Birch Town, 13 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are accessible at the vacation home free of charge. The vacation home is composed of 2 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 49 miles from the property.

Amenities:

Internet • Other • Air Conditioner • Parking • Child Friendly • Fireplace/Heating • Security/Safety

Sand Dollar Villa
Villa
Chincoteague, Virginia, USA

THE REEF VACATION VILLAS INCLUDE THE FOLLOWING FOR OUR GUESTS:
*All units sleep 6
*Daily and Weekly Rentals Available
*Full Kitchen
*Use of Inclusive Indoor Pool
*Free Wifi
*4 FREE Maui Jack Waterpark passes (Seasonal)
*Free Bike Rentals
*On-Site Grills and picnic area
*Free Parking
We are located just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse. This 2 Bedroom, 1.5 Bath Villa sleeps 6 and features a full kitchen with pots, pans, utensils, dishes and drinkware, toaster, coffee pot, microwave, refrigerator/freezer and oven. To make your trip to paradise even easier, we've included bed and bath linens, toilet paper, paper towels, trash bags and dish soap. Your Villa provides 2 parking spaces.

Complimentary washers & dryers are located on property. Heated indoor pool is open April thru November.
Close to the Beach...... Close to PERFECT!

Guest Reviews:

- "The property was as expected. The only complaint is that there were no simple items like soap and shampoo that would normally be available at a hotel or resort." - "Came home to visit family with my wife and baby. The place had everything we needed and the indoor pool was a nice place to cool off out of the sun." - "Loved the location. Loved the pool. Loved the tickets to water park. Bikes were fun. Very helpful landlord. Perfect place to get all the perks of Chincoteague island"

Channel Watch - Waterfront home with private Pier!
House
6397 Pine Drive, Deep Hole, VA, 23336, USA

Channel Watch - Waterfront home with private Pier! offers accommodations in Deep Hole, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Internet • Child Friendly • Fireplace/Heating • Other • Parking • Air Conditioner • Security/Safety

The Porpoise of Life - Spectacular Brand New Waterfront!
House
Chincoteague Island, Virginia, USA

Have you ever asked yourself what the purpose of life is? Here at Seaside, we believe it’s all about spending time with those that matter most, and making memories you’ll cherish forever. And if you can make the time, we’ve got the most amazing home to tell you about…..

Welcome to The Porpoise of Life in the very heart of Chincoteague Island. This beautiful Brand New home sits on the Waterfront on South Main - THE place to be for spectacular Sunsets, and overlooks the pristine Chincoteague Bay in the front, and Fowling Gut in the back! Stunning on both the inside and the outside, get ready to be wow’ed!

As you pull into the driveway, you can’t help but notice The Porpoise of Life’s classic Coastal Cape good looks. With multiple Decks facing the Water, just imagine sipping your morning coffee while watching Herons, Eagles, and Egrets fish for their morning meal - so peaceful. In the backyard you’ll find a Private Pier and Floating Dock over the Gut - the kids will have a blast Crabbing, and the Floating Dock makes launching your Kayak super easy. And out front, you'll find a Brand New Private Pier right on the Chincoteague Bay!

Wandering upstairs, Colors of Sand and Sea will warmly welcome you into this stunning Custom Home. You’ll love relaxing in the Living Area with Flat Screen Streaming TV and rich furnishings. You’ll sink into the Navy Leather Sectional and never want to leave - you can gaze at the Water from the sofa. There’s even a cozy Fireplace for those chilly off-season stays - one of our favorite times on our Little Island by the Sea. The Porpoise of Life’s Open Layout is perfect for how we live today - light and bright - perfect for spending time together without ever feeling crowded.

The Chef in your family will adore the Kitchen with Stainless Appliances and gleaming Quartz Countertops. It’s well-stocked and ready for family mealtime. Grab a quick bite at the Breakfast Nook before hitting the Beach, or dine in the luxurious Dining Area and take in lovely Views. Just off the Living Area, you’ll also find a Sunroom just begging for Happy Hour with a fun Surfboard Bar, tons of Games to enjoy, and absolutely breathtaking Water Views.

The Porpoise of Life sleeps 6 more than comfortably with 3 Bedrooms and 3 Full Baths. On the 1st Floor, Bedroom 1 has a comfy Queen Bed decked out in Nautical Navy and Crisp Red, and has a Flat Screen Streaming TV. There’s a Full Bath with Tub/Shower Combo convenient to this Bedroom and the Living Area.

On the 2nd Floor, you’ll find 2 luxurious Bedrooms - a Master and a Junior Master - both with King Beds, Flat Screen Streaming TV, and Private Master Baths with Double Vanities and Walk-in Showers. Bedroom 2 also has access to a Private Water View Balcony with lounging furniture and awesome Views. The Junior Master has a rustic Coastal Appeal with rich grays and browns, reminiscent of a stroll on the Boardwalk.

The Porpoise of Life is all about your Outdoor Living, as well. The kids will love exploring Fowling Gut teeming with life - oysters, fish, crabs, and more. Kick back and just “be”.

The Porpoise of Life - Sky above, Sand below, Peace within….

LINENS NOT INCLUDED, BUT LINEN RENTAL IS AVAILABLE!

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.

Guest Reviews:

- "The house was so clean and comfortable! The beds are extremely comfortable and the kitchen had everything we needed to prepare our meals. The views from the balconies were outstanding. We will definitely rent this house again!" - "The place was beautiful and new. Very clean and well stocked with anything you could need. The large deck of the front was a great place to relax and enjoy bay views. When battling some inclement weather, the bright sun room was a great place to enjoy drinks with a view still. Couldn’t have stayed in better place. Highly recommend staying here on a quieter more secluded part of the island."

Bliss On The Bay
Apartment
6206 Marsh Island Drive, #8, Chincoteague, VA, 23336, USA

Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 12 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a living room, a fully equipped kitchen with a microwave and toaster, and 1 bathroom. A TV with streaming services is available. For added privacy, the accommodation features a private entrance. Guests at Bliss On The Bay will be able to enjoy activities in and around Chincoteague, like cycling. A children's playground is also available for guests at the apartment. Salisbury-Ocean City Wicomico Regional Airport is 48 miles from the property.

Amenities:

Internet • Parking • Child Friendly • Air Conditioner • Fireplace/Heating • Security/Safety • Sports/Activities

Love and Luck on Chincoteague Island!
House
Chincoteague Island, Virginia, USA

All you need is Love and the Beach…..

Welcome to Love and Luck - possibly one of THE most adorable homes on Chincoteague Island! If you’ve been looking for the Chincoteague Charm of yesteryear, but need the Modern Amenities of today, you’ve come to the right place! They say that big things come in small packages, and Love and Luck is proof of that - and all of this less than 10 minutes from Assateague National Seashore, where our Famous Wild Ponies roam free! Assateague National Seashore is the most visited National Park in our Country - and after you visit, you’ll understand why that is!

Love and Luck is tucked on Ridge Road in the very heart of Chincoteague Island, yet feels a million miles away. Adorned in preppy pink and green, its uniqueness begins before you even enter, and we couldn’t love that more!

You’ll love kicking back in the Living Area with comfy furnishings, Flat Screen Smart TV, and muted tones pulled from Nature itself - so relaxing! If you don’t want to miss a moment of taking in that salty, sweet sea breeze, you’ll never want to leave the huge Screened Porch that lines the side of the home! With plenty of seating for all, plus a Dining Set for enjoying meals Al-Fresco, y’all are sure to fall in love with this space!

Mealtime will be a bay breeze in the spacious Kitchen with all the comforts of home. Well Stocked with all you need, there’s no need to dine out everyday - unless you want to, that is. Grill the Fresh Catch of the Day on the Grill, or whip up some cheeseburgers in paradise. And you’re just a hop, skip, and jump away from many great dining options! Dine in the comfort of AC, or wander out to the Screened Porch and listen to the Tree Frogs sing. Full Bath 1 is just off the Kitchen, and has a Walk-in Shower.

Love and Luck sleeps 6 comfortably in 2 Bedrooms, and with 2 Full Baths. Primary Bedroom 1 is on the 1st Floor - perfect for those not wanting to deal with stairs. Decked out in Nautical Navy and with a Queen Bed, it’s a restful retreat. It also has a Private Full Bath with another Walk-in Shower (no bathtubs in the house).

Wandering upstairs, you’ll find Bedroom 2, which sleeps 4 people. There is a comfy Queen Bed, plus a Twin Bed with Twin Trundle. This large room is light and bright, and feels like its own private getaway. There is no Full Bath on this level.

Love and Luck - the perfect place to Relax and Reconnect with those who matter most in this life........

Seaside Vacations does not allow group rentals or rent to guests under age 25 - Families only - No HS Senior Groups, Bachelor-Type Parties, etc. Therefore, online bookings for group rentals will not be honored.

Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any error.

Guest Reviews:

- "It was very nice n clean!! The host was very friendly n accommodating!!" - "Love and Luck provided us with a perfect family getaway. It was perfect for our needs and exactly what we wanted. Will definitely stay again! Thanks for an amazing weekend! " - "We really enjoyed our visit to Love and Luck on Chincoteague Island! The screened in porch was perfect for chatting over coffee and breakfast with a lovely cross breeze. And the fan was perfect for the extra humid days :) Easy walk to trolley stops, parks and water views. "

No Problem
House
6163 Marsh Island Drive, Chincoteague, VA, 23336, USA

Free Wifi is available throughout the property and Mid-Atlantic Regional Spaceport is 12 miles away. The air-conditioned vacation home is composed of 2 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. A TV with streaming services is featured. For added privacy, the accommodation features a private entrance. Guests at No Problem will be able to enjoy activities in and around Chincoteague, like cycling. A children's playground is also available for guests at the vacation home. Salisbury-Ocean City Wicomico Regional Airport is 48 miles away.

Amenities:

Internet • Security/Safety • Guest Services • Oceanfront • View • Parking • Barbecue/Outdoor Cooking • Sports/Activities • Child Friendly • Ocean View • Fireplace/Heating • Air Conditioner

Fiddler Bay #5
House
Chincoteague, Virginia, USA

Well-appointed, comfortable townhome with stunning views of Assateague and Lighthouse.
Enjoy the shared pier for canoeing and crabbing.
The first floor features the living room, kitchen, and dining area.
Also on first level is a private den with a full bath and queen sleeper sofa.
The second floor has two bedrooms, each with a private bathroom.
The rear bedroom is waterfront with a king bed and a balcony overlooking Assateague Channel.
The front bedroom has a queen bed.
Bring your kayaks; this is an ideal location.

Guest Reviews:

- "Fantastic view of the salt marsh and bay. Townhouse was spotless and comfortable. Enjoyed our stay immensely. " - "Loved staying at this property, waking up to the sun rising over the marshlands, seeing the lighthouse from the bedroom, watching birds on the water and kayakers gliding by. Plenty of space and balconies on both sides of the building. " - "This house is absolutely wonderful. It is spacious, with more than enough room for my family of 5. It is well-equipped, with everything we needed for cooking meals. And the views were incredible! We loved looking across the channel to the lighthouse from the deck and from inside the house. We loved watching hummingbirds, egrets, ospreys and more. And the dock was an idyllic place to watch beautiful sunsets over the marsh each night. We hope to stay here again!"

Tall Pines - Pet friendly with screened porch!
House
5328 Oak Drive, Deep Hole, VA, 23336, USA

Tall Pines - Pet friendly with screened porch! offers accommodations in Deep Hole, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home is composed of 2 bedrooms, a fully equipped kitchen, and 1 bathroom. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Pet Friendly • Security/Safety • Child Friendly • Parking • Fireplace/Heating • Internet • Air Conditioner • Other

Sea Star-Views of the Lighthouse!
House
Chincoteague, Virginia, USA

Well appointed townhouse complete with sunrises over Assateague Channel and boat docking at your door.

Comfortable living room features stunning views and seasonal gas fireplace.

Beautiful hardwood floors throughout main level open floor plan. Half bath off of kitchen.

Upper level features waterfront master bedroom with queen bed, private bath and balcony.

Second bedroom has two twins and full bath access in hallway.

Deep water dock for your boat, kayak and crabbing.

Guest Reviews:

- "Perfect location, great amenities, beautiful view." - "We were unsure whether to book Sea Star. The listing was almost completely devoid of details, and there were no reviews. But it was wonderful, and we had a great visit. And the view of the lighthouse across Assateague Channel was amazing. The queen bed was comfortable, just a little on the stiff side, and that's something that's important to us." - "We had a great time on Chincotague staying at the Sea Star. It was in the perfect location for views of the lighthouse and to watch the activity on Assateague Channel. We spent lots of time at the NWR hiking, biking, and photographing. It was nice to come back to a comfortable condo at the end of a busy day. Thanks for opening up this home to us. *Note - we didn't realize that towels (bath or kitchen) were not provided - perhaps that is normal for Chincoteague rentals? We didn't see this on the original VRBO listing, so if you plan to come, grab a set of your own towels. :)"

Shell Cottage - Pet friendly, Hot tub, Fenced yard!
House
7703 East Side Road, Birch Town, VA, 23336, USA

Shell Cottage - Pet friendly, Hot tub, Fenced yard! offers accommodations in Birch Town, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home includes 4 bedrooms, a fully equipped kitchen with a dishwasher and an oven, as well as a kettle. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Pet Friendly • Child Friendly • Internet • Air Conditioner • Other • Fireplace/Heating • Security/Safety • Parking

Escape at Deep Hole Hideaway - Pet friendly duplex!
House
Chincoteague Island, Virginia, USA

Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind? We've got you covered! Our chic and well-equipped living space will make you feel right at home. And when your tummy rumbles, our kitchen is your culinary sanctuary. Two snug bedrooms await you, furnished with a Queen bed, a Twin daybed, plus a sleeper sofa for your whole posse! The elegant and refreshing décor will overwhelm you with happiness as soon as you step through the front door!

- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Guest Reviews:

- "My family and I had a wonderful stay here at Escape! Modern, clean, private, and safe neighborhood. We enjoyed the smart tv in the evenings after a day of fun at the beach and made use of the fire pit to make s’mores and toast shrimp a few times, as well. Plenty of pillows and blankets to cuddle up with and comfortable furnishings. ‘Escape’ definitely felt like a home away from home! " - "Very quiet, clean property, close to everything."

The Haven - Waterfront with private dock!
House
7544 East Side Road, Birch Town, VA, 23336, USA

The Haven - Waterfront with private dock! offers accommodations in Birch Town, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 3 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Fireplace/Heating • Other • Internet • Air Conditioner • Security/Safety • Parking • Child Friendly

Miss Ida- Adorable Downtown Historic Cottage w/Screened Porch
House
Chincoteague, Virginia, USA

Miss Ida is a newly constructed replica of a typical 1920's single-story Chincoteague home. A stunning blend of modern amenities and traditional styling provides extraordinary and luxurious comfort for guests.
The traditional Chincoteague 1920's architecture of Miss Ida
along with the wonderful antique furnishings and decor will transport you back to a bygone era.

The queen bedroom and a second bedroom with two twins share the adjacent full bathroom.

Rear screened porch or front porch...

Great outdoor space at this unique Chincoteague home.

The queen bedroom has a private half bath.

The second bedroom with two twins is adjacent to a full hallway bath.

Rear screened porch or front porch...

great outdoor space at this unique Chincoteague home.

For larger groups, this house can also be rented with neighboring Myrtle on Mumford.

Guest Reviews:

- "We enjoyed our week's stay in the Miss Ida cottage for pony penning week. The modern kitchen made meal preparation easy. Living room seating was plentiful and comfortable. The queen bed was extremely comfortable and the bath and a half were clean and modern. Amidst the modern conveniences the cottage was decorated with Victorian era pieces and actual photos of Misty and Clarence Beebe. The location was conveniently located to Main Street and the Carnival grounds so walking down to watch the ponies parade up Main to the grounds was ideal. Miss Ida was a lovely place to stay and i recommend it when visiting Chincoteague Island."

Windshadow - Waterfront & pet friendly!
House
4635 Main Street, Deep Hole, VA, 23336, USA

Both free Wifi and parking on-site are available at Windshadow - Waterfront & pet friendly! free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation has a fireplace. Salisbury-Ocean City Wicomico Regional Airport is 48 miles away.

Amenities:

Air Conditioner • Fireplace/Heating • Internet • Pet Friendly • Other • Security/Safety • Parking • Child Friendly

Tranquility - Brand new home in quiet location!
House
Chincoteague Island, Virginia, USA

Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring 4 bedrooms, 2 bonus rooms and 2.5 baths. Sleeps up to 11 with 1 king, 2 queens, 2 queen conversion sofa/sleepers and a twin fold-out sleep chair. Deep Hole Hideaway rental properties can accommodate up to 23 people by renting all 3 units in this complex! (based upon availability) Tranquility Great for family reunions or large gatherings! Please reach out to our office or check out "Escape at Deep Hole " and "Serenity at Deep Hole" for multi home bookings.

Pet friendly, private and quiet. This property allows for entertainment and relaxation for both you and your kids! There is also outdoor seating, cornhole, a firepit, picnic tables and barbecues for additional recreation for your vacation. Book your stay today, this one won't last long!

- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Guest Reviews:

- "We were excited for have a lovely 4 day stay on Chincoteague Island and found the Tranquility home overall perfect for our group of 4 adults and one dog. With being a new home (still smelled like a new build!) the house was well appointed with beach decor, a brand new kitchen with any appliance you could need, plus ample bedrooms/bathrooms for everyone. Tucked away off of Deep Hole Rd, the location was perfect - close to everything while also not being on the busy main streets. There were a few changes we’d recommend: there was no full length mirror in the home, which would have been a nice addition. There was a cute front porch and a back porch but only one (very uncomfortable) bench on the front porch that could only fit two people. Would be great to have additional porch furniture to sip morning coffeees or cocktails on. While each bathroom had a small trash bag in it on arrival, it would have been nice to have extra small trash bags. We ended up going out and buying our own. There was also a small oversight with our outside trash bin never arriving so we had to take our trash up to the trash/recycling station across the street. We also never received the WiFi password and needed to ask for those details after our arrival. These are such small inconveniences that were easily overcome and it not impact the quality of our stay. Overall we highly recommend the home! Additionally the property management company was fabulous! They were so quick to answer any and all questions w"

Sunset Bay Villa 312 - Waterfront & includes a boat slip!
House
6321 Captain's Lane #312, Chincoteague, VA, 23336, USA

13 miles from Mid-Atlantic Regional Spaceport in Chincoteague, Sunset Bay Villa 312 - Waterfront & includes a boat slip! provides accommodations with access to a fitness room. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 49 miles away.

Amenities:

Fireplace/Heating • Internet • Air Conditioner • Wellness Facilities • Child Friendly • Parking • Security/Safety • Other

Flamingo Villa
Villa
Chincoteague, Virginia, USA

THE REEF VACATION VILLAS INCLUDE THE FOLLOWING FOR OUR GUESTS:
*All units sleep 6
*Daily and Weekly Rentals Available
*Full Kitchen
*Use of Inclusive Indoor Pool
*Free Wifi
*4 FREE Maui Jack Waterpark passes (Seasonal)
*Free Bike Rentals
*On-Site Grills and picnic area
*Free Parking
We are located just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse. This 2 Bedroom, 1.5 Bath Villa sleeps 6 and features a full kitchen with pots, pans, utensils, dishes and drinkware, toaster, coffee pot, microwave, refrigerator/freezer and oven. To make your trip to paradise even easier, we've included bed and bath linens, toilet paper, paper towels, trash bags and dish soap. Your Villa provides 2 parking spaces.

Complimentary washers & dryers are located on property. Heated indoor pool is open April thru November.
Close to the Beach...... Close to PERFECT!

Guest Reviews:

- "just walk across the street" - "We were on the shore for a wedding and it was fun being a tourist on Chincoteague for a weekend. Plenty of fun things for an 8 year old to do."

An Unfettered View - Beautiful ranch w/boat dock!
House
6254 Wagner Lane, Deep Hole, VA, 23336, USA

Both free Wifi and parking on-site are accessible at An Unfettered View - Beautiful ranch w/ boat dock! free of charge. The vacation home is composed of 2 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 49 miles from the property.

Amenities:

Internet • Security/Safety • Fireplace/Heating • Other • Child Friendly • Air Conditioner • Parking

Sandpiper Shanty - Brand New and Dog Friendly!
House
Chincoteague Island, Virginia, USA

A day spent at the Beach is never a wasted day….

Welcome to stunningly beautiful and Brand New Sandpiper Shanty on Chincoteague Island, located in the very heart of our Little Island by the Sea! This amazing Custom Home was just completed in August 2025, and is the sister house to ever-popular Seahorse Shanty, almost right next door! And if you can believe it, it is every bit as gorgeous, and also welcomes your well-trained dog (2 max) at no additional cost - because hey, dogs are family, too! And its great mid-Island location means you’re less than 10 minutes from Assateague National Seashore, where our famous Wild Ponies roam free!

As you enter Sandpiper Shanty, you’ll be swept away by the Colors of Sand and Sea, beachy flooring reminiscent of a stroll on a rustic boardwalk, and its gorgeous decor. Kick off your Flip Flops and let the fun begin….

The spacious Living Area is perfect for kicking back after a fun-filled day at the Beach and enjoying Free WiFi and Flat Screen Smart TV. With comfy seating for all, it’s a wonderful place to gather and share stories of the day’s adventures. There’s even a cozy Fireplace for those chilly Off-Season Stays - one of our favorite times here on Chincoteague! Adorned in high-end furnishings and tons of original art, it encompasses everything we love about our Island.

Just off the Living Area is the Well-Stocked Kitchen and Dining Area, both of which will thrill the Chef in your family! With Stainless Appliances, Quartz Countertops, and a HUGE Center Island with lots of seating, it truly is a dream Kitchen. Dine in the comfort of Central AC in the Dining Area, or on the Screened Porch, surrounded by Shade Trees, and take in that salty, sweet sea breeze. And ahhh, you can almost hear the breeze rustling the tall Pines, can’t you?

Sandpiper Shanty is perfect for a large family, or 2 families to share, and sleeps 10 in pure comfort and style. The Primary Bedroom is located on the 1st Floor,and is dressed in serene Coastal Colors and a Sandpiper Theme, sure to bring a restful night’s sleep. With a Walk-in Closet, Flat Screen TV, and Attached Full Bath, it’s made for sweet dreams. In the Attached Full Bath, you’ll find a gorgeous Double Vanity and Walk-in Shower. Also on the 1st Floor is a Half Bath, which is convenient to the Living Area and Kitchen.

Wandering upstairs, you’ll find 2 more Bedrooms, plus a Bonus Bunk Room. Bedrooms 2 and 3 are decked out with comfy Queen Beds, beautiful Bedding, and Flat Screen Smart TVs. The Bunk Room will thrill the kids with 2 sets of Twin Bunkbeds (sleeping 4 total) and huge Barn Doors. Another Full Bath with Tub/Shower Combo is upstairs and convenient to all Bedrooms.
All of this, and only a few miles from the Beach! Whether you enjoy fishing, shell-combing, or searching for ponies, Assateague has something for everyone, and is hands down one of the most stunning, natural beaches in America - no boardwalks, no shops, just Mother Nature at her finest.

Owner has exterior security camera. Friendly Dogs welcome at no additional fee and must be approved in advance - 2 max and current on Vaccinations and Flea/Tick Preventative.

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.

Amenities:

Fireplace/Heating • Kitchen • Accessibility • Pet Friendly • Other • Balcony/Terrace • Air Conditioner • Laundry • Internet • Sports/Activities • Tv • Security/Safety

Whispering Pines
House
8165 Marsh Point Lane, Black Point Landing, VA, 23336, USA

Whispering Pines offers accommodations in Black Point Landing, 15 miles from Mid-Atlantic Regional Spaceport. This vacation home features air-conditioned accommodations with a patio and free Wifi. Guests can use a garden. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. A TV with streaming services and a DVD player are available. The accommodation has a fireplace. For guests with children, Whispering Pines provides a children's playground. Guests can also warm up near the outdoor fireplace after a day of cycling. Salisbury-Ocean City Wicomico Regional Airport is 51 miles from the property.

Amenities:

Security/Safety • Barbecue/Outdoor Cooking • Child Friendly • Sports/Activities • Pet Friendly • Parking • Fireplace/Heating • View • Internet • Air Conditioner

Carriage House
House
5216 Pine Tree Way, Deep Hole, VA, 23336, USA

Providing a garden, Carriage House provides accommodations in Deep Hole. Guests can benefit from a patio and a children's playground. This pet-friendly vacation home also has free Wifi. The air-conditioned vacation home is composed of 4 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 3 bathrooms. A TV with streaming services and a DVD player are featured. The accommodation has a fireplace. Guests at the vacation home will be able to enjoy activities in and around Deep Hole, like cycling. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Security/Safety • Internet • Fireplace/Heating • Air Conditioner • Pet Friendly • View • Parking • Sports/Activities • Child Friendly • Barbecue/Outdoor Cooking

Island Sunrise - Pet friendly, waterfront duplex!
House
6423 Pine Drive, Deep Hole, VA, 23336, USA

Island Sunrise - Pet friendly, waterfront duplex! offers accommodations in Deep Hole, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are accessible at the vacation home free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles from the property.

Amenities:

Other • Security/Safety • Child Friendly • Fireplace/Heating • Parking • Air Conditioner • Internet

Sunset Dreams - Pet friendly, Waterfront, & shared dock!
House
3066 Main Street, Black Point Landing, VA, 23336, USA

Sunset Dreams - Pet friendly, Waterfront, & shared dock! offers accommodations in Black Point Landing, 15 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are accessible at the vacation home free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles from the property.

Amenities:

Security/Safety • Pet Friendly • Other • Fireplace/Heating • Parking • Internet • Child Friendly • Air Conditioner

Southern Exposure - Waterfront with boat dock!
House
7005 Pine Drive, Deep Hole, VA, 23336, USA

Southern Exposure - Waterfront with boat dock! offers accommodations in Deep Hole, 14 miles from Mid-Atlantic Regional Spaceport. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home is composed of 4 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles away.

Amenities:

Fireplace/Heating • Air Conditioner • Security/Safety • Internet • Child Friendly • Other • Parking

Sea Oats - Water front with boat dock!
House
5361 Pearl Drive, Deep Hole, VA, 23336, USA

Both free Wifi and parking on-site are accessible at Sea Oats - Water front with boat dock! free of charge. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. Salisbury-Ocean City Wicomico Regional Airport is 50 miles from the property.

Amenities:

Other • Security/Safety • Air Conditioner • Child Friendly • Fireplace/Heating • Internet • Parking

Crabby Pines - Pet friendly modern accommodations!
House
Accomack County

Welcome to "Crabby Pines!" - a fabulous vacation home located on Chincoteague Island! Enjoy all the fine features this charming ranch-style has to offer, and remember, you're renting the *entire* place which means you don't have to share! After all, this is... #WhereGreatVacationsHappen ...on Virginia's Eastern Shore!

The space
Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.

Enjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly? Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.

This welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while still exuding a sense of warmth and comfort. The property's easy access to local amenities, combined with its peaceful surroundings, makes it an ideal choice for anyone looking for a balance between nature and community activities.

Whether you're settling down with family or looking for a tranquil spot to return to after a day of adventures on the island, this home is sure to meet your needs. Embrace a laid-back lifestyle in Chincoteague with this delightful vacation home opportunity.

Guest access
The door access code will be emailed prior to your arrival date, as well as texted to the number on file on the day of arrival.

Other things to note
- No smoking is permitted on the premises.
- Linens and towels are included with your reservation.
- This home is pet friendly with an additional fee. Maximum of two dogs under 25 lbs. each; no cats.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Amenities:

Hot water • Smoke alarm • Hangers • Air conditioning • Dryer • Fire extinguisher • Washer • Heating • Cleaning products • TV

Assateague Inn 104S is an adorable Studio that
House
Accomack County

Relax and unwind at The Assateague Inn on Chincoteague Island. Assateague Inn 104S is an adorable Studio that sleeps 4 with lovely water views and an Outdoor Pool.

The space
Linens Included. Seasonal Outdoor Pool. No Smoking/No Pets

Guest access
Guests will have access to their private suite, the community pool, and wonderful waterfront dock. There is also a picnic area with tables and charcoal grills for your use!

Other things to note
Mmmmm., Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible.

Welcome to Assateague Inn 104 - Newly Renovated and absolutely adorable. With New Flooring and Updated Furnishings, it’s a wonderful beach getaway! Decked out in cool Coastal Grays and Crisp Whites, it’s serene and peaceful. Perfect for couples or a small family, you can have that beach getaway you’ve been longing for - all without breaking the bank!

Assateague Inn 104 has a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. The Updated Kitchen has all you need for a quick bite before exploring Assateague National Seashore, with cookware and dishes, 2 burner stove top, mini refrigerator AND a full size refrigerator, coffee maker, toaster and eating area.

You’ll love relaxing on the Community Pier with gorgeous Views, or try your hand at Crabbing and Fishing! You can also end each precious day with a dip in the seasonal Outdoor Pool, or grill some cheeseburgers in paradise in the Picnic Area complete with Charcoal Grills.

Tucked just off of Maddox Boulevard - aka the Beach Road - you can take a short stroll or bike ride to Mini Golf, Dining, and of course, Assateague National Seashore! When you're not enjoying playing on the waterfront, relax on the huge landscaped greens with plenty of Picnic Tables and Barbecue Stations to cook up the Fresh Catch of the Day.

Whatever your pleasure on beautiful Chincoteague Island, the Assateague Inn is the perfect home base. Give us a call and let us help you plan your Adventure today!

Assateague Inn 104S - Chincoteague Island is calling!

*Seasonal Outdoor Pool - dates subject to change*

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.

Les Bon Temps on Chincoteague Island!
House
Accomack County

Les Bon Temps is a beautiful 3 Bedroom/2 Bath Vacation Rental on Chincoteague Island. This lovely home is only steps to the Community Boat Launch, making it great for boaters and kayakers alike!

The space
LINENS INCLUDED

Other things to note
New Screened Porch, Expanded Sunroom, New Front Deck, and Electric Vehicle Charger!

"Les Bon Temps" loosely translates to "Let the good times roll" - can you think of a better phrase to kick off your Chincoteague Island Vacation this year? Tucked away on the East Side, this quintessential Chincoteague Cottage is beyond charming.  Located only steps from the Public Boat Launch and amazing Views of the Assateague Lighthouse, Les Bon Temps is the perfect place for kayakers, boaters, and nature lovers. Traveling with a large family or several families together? Be sure to check out her Sister House, Rhythm and Blues, right next door - the perfect way to have lots of togetherness, while still having privacy.

Life at Les Bon Temps is truly laid back.....relax on the Brand New Deck and take in those salty, sweet bay breezes. There's nothing like the smell of Low Tide on our little piece of Paradise. Stroll down to the end of the drive to take in astonishing Bay and Assateague Lighthouse Views, and it's an easy walk to very popular Memorial Park. Bring your kayaks or small boat to drop in at the Community Boat Launch just across the street and paddle out to explore one of our Sand Bars or do some fishing. Don't have kayaks? No worries, we are here to help you plan your Chincoteague Adventures - just give us a call!

As you enter Les Bon Temps, you'll fall madly in love with the newly expanded Sunroom, which lines the front of the house. With gleaming new floors, huge windows, and all new furnishings, you're sure to spend a lot of time here. Walking into the Living Area, you'll be amazed at how light, bright, and spacious this beautiful Vacation Home is. Soaring Warm Wood Ceilings and a carefree Open Floor Plan welcome you and let you know right away what a fabulous stay you're about to have. 

Relax after a fun-filled day of exploring Assateague, sink into the comfy Living Room Furniture, and enjoy the Flat Screen Smart TV and Free WiFi. The Living Area opens to the huge Kitchen with Dining Area. There is plenty of room at the Dining Table for all, and the Chef in your family will love preparing meals in this very Well-Stocked Kitchen. You can even grill the Fresh Catch of the Day and dine Al-Fresco on the Brand New Screened Porch with Dining Table and Chairs.

Les Bon Temps sleeps 6 very comfortably with 3 Bedrooms and 2 Full Baths. The theme throughout this breathtaking home is pure fun - enjoy life to the fullest and make every moment count. That's easy to do here on our little slice of heaven. In Bedroom 1, you'll find 2 Twin Beds and soothing Beachy Blues. Down the hall, Bedroom 2, which is the Master, has a fabulous Queen Bed and lots of space. You'll love the Master Bath with Tub/Shower Combo. The Lofty Warm Wood Ceiling makes this space feel enormous. Just across the hall, Bedroom 3 has another Queen Bed and is beautifully decorated with Bold Reds and Beachy Blues. There is another Full Bath with a Tub/Shower Combo conveniently located down the hall, as well. 

The Outdoor Living Space is every bit as wonderful at Les Bon Temps. Toast marshmallows and share fish tales around the large Shared Fire Pit. Wander down to the Boat Launch and try your hand at crabbing or fishing. Sister House, Rhythm and Blues, is right next door - together these 2 homes will sleep 13 people, making it a wonderful choice for several families traveling together or a family reunion. Time shared around the Fire Pit is sure to make some awesome new Vacation Memories for all!

Life is short - Les Bon Temps - Let the Good Times Roll right here on Chincoteague Island!

Seaside Vacations does not allow group rentals to guests under age 25.  Therefore, online bookings for group rentals will not be honored..

Amenities:

Fire extinguisher • TV • Bed linens • Washer • Indoor fireplace • Extra pillows and blankets • Smoke alarm • Dryer • Heating • Air conditioning

Fern's Cottage-Renovated,In Town, Perfect Location
House
Accomack County

Just a few miles from Chincoteague National Wildlife Refuge & Assateague Island Beach, Fern's Cottage is a beautifully renovated Chincoteague Island Cottage
Great In-Town location - close to shops, restaurants, waterfront park, & public fishing pier
This charming cottage features:
Lovely eat-in kitchen is fully equipped with all amenities
Cozy living room featuring full sleeper sofa and recliner
Queen bedroom with adjacent full bathroom
Large front porch perfect for outdoor dining

Guest access
Entire home.

Other things to note
There is no washer and dryer at the unit. Local laundromat has very limited hours.

Amenities:

Bathtub • Clothing storage • Room-darkening shades • Ethernet connection • Iron • Bed linens • Hot water • Hair dryer • Free dryer – In unit • Free washer – In unit

Eastwinds 18 is a fabulous 2 Bedroom Pet-Friendly
House
Accomack County

Eastwinds 18 is a fabulous 2 Bedroom Pet-Friendly Townhome in the very heart of Chincoteague Island. Surrounded by Whispering Pines, it`s just the perfect home base for your Chincoteague Island Adventures.

The space
DOGS WELCOME WITH $100 PET FEE EACH - Please let us know if you will be bringing your Dog when making your Reservation
LINENS INCLUDED, NO SMOKING, NO VAPING. FAMILIES ONLY AND MUST BE AT LEAST 25.

Guest access
Entire House, yard, and waterfront lot located directly across Main Street.

Other things to note
Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 18, located in the very heart of Chincoteague Island. This lovely Townhome is convenient to everywhere you want to be on our beautiful Island, yet a quiet and peaceful Retreat at the day's end. And, there's no need to leave Fido out of the fun - Eastwinds 18 is Dog and Cat Friendly!


Eastwinds is a small community of townhomes surrounded by Whispering Pine Trees just off of Church Street, which offers easy access to everything you love about our Island. Only minutes from the beach, downtown shops and restaurants, and more, it's Vacation Central, for sure!  As you wander down the path to Eastwinds 18, you'll feel the serenity of the trees swaying in the salty air and that wonderful feeling of calmness that overtakes you when you realize you're finally HERE. 

This lovely home is warm and well appointed. As you enter Eastwinds 18, you cannot wait to relax on the shaded Front Porch with your morning coffee. The Living Area is warm and welcoming with comfy furnishings, beachy floors reminiscent of a boardwalk, and lots of Local Art. Relax after a fun-filled at exploring Assateague, and enjoy the Central AC, Free WiFi, and Flat Screen Cable TV. Decorated with a Coastal Flair, it's a fun place to unwind even when you're not at the beach!

The Chef in your family will love the huge Kitchen that has everything you need to make mealtime a bay breeze. There's plenty of room at the spacious Dining Table for everyone to relax and reconnect. Just off the Kitchen is a wonderful Screened Porch - the perfect place to share stories of the day's adventures. There's also a convenient Half Bath just off the Living Area. 

Upstairs you'll find 2 spacious Bedrooms and 2 Full Baths! The Master has a comfy Queen Bed, and its own Private Covered Porch complete with 2 Rocking Chairs with your name on them! There is also a Private Full Bath with Tub/Shower Combo. Right down the hall, Bedroom 2 is a breath of fresh air in colors of Sea Glass and Coral. There is a Full and Twin, plus a Twin Sleeper Chair - a perfect room for the kids! There is also another Full Bath with Tub/Shower Combo, so no waiting in line after a day of sun and fun!

Eastwinds 18 is awesome in that it welcomes your well-trained dog with a $100 Pet Fee *per pet*. This is a wonderful area to enjoy long walks with your four-legged friend, and they will love you even more for bringing them along!

Eastwinds 18 - Happy People. Happy Pets. Happy Vacation!

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee per pet. Dogs MUST be current on Flea/Tick Preventative and Immunizations. No Cats.

Amenities:

Smoke alarm • Washer • Hair dryer • Bed linens • Heating • Iron • Extra pillows and blankets • TV • Dryer • Air conditioning

Painted Pony Cottage - A short stroll from the
House
Accomack County

Painted Pony Cottage is a delightful Pet-Friendly Vacation Rental on Chincoteague Island. Located in the heart of the Island, you will love being able to walk to the Carnival Grounds!

The space
DOGS WELCOME WITH $100 PET FEE EACH and must be preapproved. Please let us know if you will be bringing your Dog when making your Reservation.

Guest access
Entire House and beautiful fenced-in yard.

Other things to note
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Painted Pony Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chincoteague Island Vacation Memories. 

As you pull up to this whimsical Cottage, the White Picket Fence and Sea Glass Blue Door are so welcoming. You can already feel yourself relaxing. Just the thought of sipping Sweet Tea on that Screened Porch - you can hardly wait. Located in the heart of Chincoteague Island on Willow Street, you are tucked away in a quiet location, yet close to everywhere you want to be. Walk to the Carnival Grounds in July to enjoy our famous Firemen's Carnival, and visit the ponies penned up just a short walk from the Cottage. 

There is ample parking for 3 Cars just behind the house, off of Willow Street. As you enter Painted Pony Cottage, fond memories of Grandma's house may come back to you - it just feels so comfy and full of love. The spacious Kitchen has Warm Knotty Pine Cabinets and lots of Countertop space. The Chef in the family will be pleased with how well-stocked it is. Dine indoors at the colorful Kitchen Table, or Al Fresco at the Picnic Table in the backyard - a great place to enjoy some of our Fresh Local Crabs! 

As you wander to the Living Area, you'll fall madly in love with the Rustic Hardwood Floors throughout the Cottage. Relax after a fun-filled day at the Beach in the AC, and enjoy the Free WiFi and Flat Screen Streaming TV. Colors of Sunshine and Blue Sea are so bright and cheerful - it's just a great room to spend time in. Just off the Living Area lining the front of the Cottage is a fabulous Screened Porch with relaxing Rockers and Gliders - a wonderful place to gather in the evening and share stories of the day's adventures. Watch the kids play safely in the Fenced-in Front Yard, which Fido will appreciate, as well!

Painted Pony Cottage sleeps 6 more than comfortably in 3 Bedrooms, with a Full Sleeper in the Living Area. The Master Bedroom is on the 1st Floor and is also the only access to the Full Bathroom. Adorned in Nautical Navy and White, it is bright and cheerful, and has a comfy Full Bed. The shared Full Bath has a Tub/Shower Combo, and although you access it through the Bedroom, it is quite convenient for all. Fun painted pony decor greets you, keeping this awesome theme going throughout the Cottage. Watch your head as you follow the Winding Wood Stairs upstairs to Bedrooms 2 and 3. There are 2 Twins in Bedroom 2, and another Twin in Bedroom 3. This is an awesome place for the kids, who will feel like they have their own private hideaway. 

Painted Pony Cottage - The perfect place to Relax and Reconnect with those who matter most in this life........

Painted Pony Cottage is a Sunday - Sunday Rental during Peak Season.

 Seaside Vacations does not allow group rentals to guests under age 25.  Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee *PER PET*. Dogs MUST be current on Flea/Tick Preventative and Immunizations. No Cats.

Amenities:

Extra pillows and blankets • Hair dryer • Smoke alarm • Dryer • Iron • TV • Air conditioning • Heating • Bed linens • Washer

Safe Harbor - The Charm you love and the
House
Accomack County

Safe Harbor is an adorable Pet-Friendly Vacation Cottage in the very heart of Chincoteague Island offering the Charm you love and the Modern Amenities you need!

The space
DOGS WELCOME WITH $100 PET FEE - Please let us know if you will be bringing your Dog when making your Reservation.

Other things to note
Welcome to Safe Harbor on magical Chincoteague Island - the perfect place to relax, rewind, and reconnect. This adorable Dog-Friendly Cottage simply oozes that quintessential Chincoteague Charm you love so much, while giving you the Modern Amenities you need. Located in the heart of our Island at the corner of Chicken City and Ridge, you’re close to everywhere you want to be, yet will feel so far away from the stresses of daily life - you’re on Island Time now!

Safe Harbor feels like just that - a relaxing getaway - a place to let your troubles be forgotten. As you pull into the driveway, you’ll love the Beachy Style of Safe Harbor - Tropical Colors, inviting Landscaping, and a Patio that you cannot wait to sip Sweet Tea on. Fido is already scoping out the Fenced Yard - just perfect for a game of fetch! Kick off your Flip Flops in the Mud Room, and the good times begin…..

You’ll love taking a breather in the Living Area with Flat Streaming TV, comfy Furnishings, and Free WiFi, after a fun-filled day exploring wonderful Assateague National Seashore. Even better is relaxing on the Patio in a Rocking Chair and listening to the sea breeze rustle the shade trees. Safe Harbor’s beautiful yard is perfect for lounging and playing, and your pup will love basking in the Sun next to you,

The Chef in your family will adore the bright, updated Eat-in Kitchen with gorgeous Glass Backsplash, Granite Countertops, and Beachy White Cabinetry. Well-Stocked with all you need, preparing family meals will be no chore at all. Not one to cook on Vacation? No worries, many Dining Options, Shops, and Main Street are just a short stroll away. Just off the Kitchen, a cozy Sunroom lines the front of Safe Harbor - a great place to curl up with a good book or share stories of the day’s Adventures. There is also a Full Bath with a Tub/Shower Combo on the 1st Floor.

Wandering upstairs, you’ll find 2 Bedrooms that sleep 6 in all. Bedroom 1 has 4 Twins - 1 sets of twin bunk beds, plus two additional Twins and sleeps 4. Adorned in Sunny Yellow and Nautical Blue, it’s such a bright and cheerful space. Down the Hall, Bedroom 2 has a comfortable Queen Bed, and is decorated with cheerful Shabby Chic Style.

So, if you truly want to experience Life as a Local here on Chincoteague Island - AND bring the furriest member of your family - know that you will be in a Safe Harbor in this delight of a Vacation Home on our little slice of Heaven - See y’all soon!

Seaside Vacations does not allow group rentals to guests under age 25.  Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with no additional fee. Dogs MUST be pre-approved and current on Flea/Tick Preventative and Immunizations. No Cats.  Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.

Amenities:

Smoke alarm • Fire extinguisher • Heating • TV • Bed linens • Iron • Washer • Dryer • Wifi • Air conditioning

Fishhook Hideaway on Chincoteague Island!
House
Accomack County

This Chincoteague Island Vacation Home is both adorable AND affordable!

The space
LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

Other things to note
Sometimes you just have to go with the waves…..

Looking to catch a beach getaway at a family-friendly price? Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day! This adorable 2 Bedroom/2 Full Bath home is located in the heart of our little Island - just a short stroll from Maddox Boulevard, Steamers, and The Island Creamery, and a very short 5 minute ride to Assateague National Seashore!

Fishhook Hideaway has all you need for the perfect family getaway. You’ll love relaxing in the comfort of Central AC after a fun-filled day at the Beach, and enjoying Free WiFi and Flat Screen TV. Newly renovated and with brand new furnishings, it’s comfy and cozy. Just off the Living Area, you’ll find a Full Bath with Tub/Shower Combo, and a Full Size Washer and Dryer for your convenience. Wander up just 3 steps, and you’ll find the Well-stocked Kitchen supplied with all you need to make mealtime a bay breeze. No need to dine out every day - unless you want to!

This adorable Townhome sleeps 7 in comfort and style. Wandering upstairs you’ll find 2 beautifully decorated Bedrooms and a Full Bath. Bedroom 1 has a comfy King and is adorned in Colors of Sand and Sea. Bedroom 2 sleeps 5 with a Pyramid Bunk (Twin over Full) and a Full Bed - just perfect for the kids!

Don’t wait - book your island time today at Fishhook Hideaway - don’t let this be the one that got away! We just know you’ll be hooked!

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.

Amenities:

Washer • Iron • Bed linens • Fire extinguisher • Heating • Dryer • Smoke alarm • Wifi • TV • Air conditioning

Mini Slice of Island Heaven
Apartment
Chincoteague

This special place is close to everything, in the heart of historic downtown. Walk to restaurants, entertainment, and shopping. 10 minute drive to Wildlife Refuge and beach! Our mini slice of heaven is the perfect size for 1 to 2 travelers. Convenience and comfort of a full kitchen, queen size bed, WiFi, TV, full size bathroom, access to laundry on site, and a coffee shop, boutique, and gourmet market on the bottom floor. Local owners excited to host & share the beauty of this amazing island!!

Amenities:

Iron • Body soap • Cleaning products • Dryer • Washer • Hangers • Shampoo • Conditioner • Hot water • Clothing storage: closet and dresser

Private Upstairs at Isle Pines with Waterview
House
Accomack County

The upstairs of this 3 bedroom, 2 bath home located in the Oyster Bay 1 private community is all yours. This includes a full bath that is for your private use. Downstairs includes shared spaces of kitchen, living room, and screened-in porch. Use of inflatable kayak available with a short walk to the canal that leads to Assateague Channel.

My partner and I live and work from home on the first floor with two cats that will be kept away from you.

Chincoteague Landmarks on the Map

Compare the Best Landmarks in Chincoteague – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Channel Bass Inn and Restaurant 6228 Church Street, Chincoteague, VA, VA 23336 220 4.0 8.8 97 Click here
Blufin Bungalows & Marina 2477 Main St, Chincoteague, VA, 23336, USA 189 3.0 9.6 205 Click here
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi 5386 Main Street, Chincoteague, VA, 23336, USA 254 4.0 8.1 10 Click here
Chincoteague Apartment w/Deck: Walk to Waterfront 6294 Cropper St, Chincoteague, VA, 23336-2420, USA 127 3.0 1 Click here
Chincoteague Townhome with Pony Views from Deck! Chincoteague, VA, USA 136 4.0 8.4 9 Click here
Misty Mare Townhouse - Gorgeous home on Chincoteague Island Chincoteague, Virginia, USA 106 2.0 10.0 11 Click here
Beach Bay Pony Place with Ponies 1 Mi to Water! Chincoteague, VA, USA 201 4.0 10.0 2 Click here
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now! Chincoteague, Virginia, USA 250 2.0 10.0 6 Click here
Horseshoe Haven 7111 Horseshoe Drive, Chincoteague, VA, VA 23336, USA 178 4.0 9.0 1 Click here
3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room Chincoteague, Virginia, USA 274 2.0 10.0 3 Click here
Key West Cottages 4251 Main Street, Chincoteague, VA, VA 23336 408 3.0 9.6 339 Click here
Josie's Getaway - Pet Friendly -Mini-Vacations and Month to Monthly Available Chincoteague, Virginia, USA 175 10.0 79 Click here
Blufin Bungalows & Marina 2477 Main Street, Chincoteague, VA, VA 23336, USA 370 3.0 9.2 111 Click here
Your Memorable Island Vacation Starts Where the Sidewalk Ends! Chincoteague, Virginia, USA 164 10.0 46 Click here
Chincoteague Bay RV Resort & Cottages 2272 Main Street, Chincoteague, VA, VA 23336, USA 349 3.0 9.0 61 Click here
Hancock House -Single Family Home - Screened Porch, NO LINENS PROVIDED Chincoteague, Virginia, USA 163 10.0 31 Click here
Chincoteague Island Cottage about 2 Mi to Beaches Chincoteague, VA, USA 494 3.0 8.0 7 Click here
An Unfettered View - Beautiful ranch w/boat dock! Chincoteague Island, Virginia, USA 397 9.8 21 Click here
Quaint Chincoteague Island Hideaway with 2 Porches! Birch Town, VA, USA 112 3.0 7.6 5 Click here
Cypress Cottage -Waterview-TOWN LINENS AND TOWELS/Beach Supplies Provided Chincoteague, Virginia, USA 148 10.0 20 Click here
3 Mi to Beach Waterfront Condo in Chincoteague! Chincoteague, VA, USA 338 3.0 10.0 2 Click here
Island Escape: Bikes, Kayaks, Grill, Firepit, Beach Gear, Large Quiet Property Chincoteague Island, Virginia, USA 208 10.0 18 Click here
Chincoteague Apartment with Deck Walk to Waterfront Chincoteague, VA, USA 111 3.0 10.0 1 Click here
CoZyQ is a 2-bedroom, 2 full baths cottage in charming Chincoteague Island, VA Chincoteague, Virginia, USA 280 10.0 12 Click here
Chincoteague Charm Escape with Bikes and Yard Games! Deep Hole, VA, USA 203 3.0 7.0 1 Click here
Oyster Bay Hideaway on Chincoteague Island! Chincoteague Island, Virginia, USA 139 10.0 10 Click here
2 Mi to Downtown Tranquil Abode in Chincoteague! Chincoteague, VA, USA 270 3.0 10.0 1 Click here
‘Beach Bay Pony Place’ w/Ponies: 1 Mi to Water! Chincoteague, Virginia, USA 178 10.0 9 Click here
Chincoteague 6360 Pine Dr, Chincoteague, VA, VA 23336, USA 292 3.0 10.0 1 Click here
Riptide’s Crossing: A waterfront getaway w/deep water dock and incredible views Chincoteague, Virginia, USA 329 10.0 8 Click here
Jellystone Park Chincoteague Island 6742 Maddox Boulevard, Chincoteague, VA, VA 23336, USA 240 7.6 20 Click here
Sunset Villa Chincoteague, Virginia, USA 141 10.0 6 Click here
Beach House @ The Reef 7023 Maddox Boulevard, Chincoteague, VA, VA 23336, USA 172 10.0 2 Click here
Pelican Sunset - Waterfront With Pier Chincoteague, Virginia, USA 266 10.0 6 Click here
Gone Coastal - Pet friendly with screened porch! 4410 Eastwinds, Birch Town, VA, 23336, USA 113 9.0 1 Click here
Sand Dollar Villa Chincoteague, Virginia, USA 285 10.0 5 Click here
Channel Watch - Waterfront home with private Pier! 6397 Pine Drive, Deep Hole, VA, 23336, USA 168 8.0 1 Click here
The Porpoise of Life - Spectacular Brand New Waterfront! Chincoteague Island, Virginia, USA 387 9.6 5 Click here
Bliss On The Bay 6206 Marsh Island Drive, #8, Chincoteague, VA, 23336, USA 197 10.0 1 Click here
Love and Luck on Chincoteague Island! Chincoteague Island, Virginia, USA 160 10.0 4 Click here
No Problem 6163 Marsh Island Drive, Chincoteague, VA, 23336, USA 293 9.0 1 Click here
Fiddler Bay #5 Chincoteague, Virginia, USA 274 10.0 4 Click here
Tall Pines - Pet friendly with screened porch! 5328 Oak Drive, Deep Hole, VA, 23336, USA 340 9.0 1 Click here
Sea Star-Views of the Lighthouse! Chincoteague, Virginia, USA 284 10.0 4 Click here
Shell Cottage - Pet friendly, Hot tub, Fenced yard! 7703 East Side Road, Birch Town, VA, 23336, USA 389 10.0 1 Click here
Escape at Deep Hole Hideaway - Pet friendly duplex! Chincoteague Island, Virginia, USA 236 10.0 3 Click here
The Haven - Waterfront with private dock! 7544 East Side Road, Birch Town, VA, 23336, USA 478 10.0 1 Click here
Miss Ida- Adorable Downtown Historic Cottage w/Screened Porch Chincoteague, Virginia, USA 245 10.0 3 Click here
Windshadow - Waterfront & pet friendly! 4635 Main Street, Deep Hole, VA, 23336, USA 440 1 Click here
Tranquility - Brand new home in quiet location! Chincoteague Island, Virginia, USA 344 10.0 2 Click here
Sunset Bay Villa 312 - Waterfront & includes a boat slip! 6321 Captain's Lane #312, Chincoteague, VA, 23336, USA 442 1 Click here
Flamingo Villa Chincoteague, Virginia, USA 399 10.0 2 Click here
An Unfettered View - Beautiful ranch w/boat dock! 6254 Wagner Lane, Deep Hole, VA, 23336, USA 443 1 Click here
Sandpiper Shanty - Brand New and Dog Friendly! Chincoteague Island, Virginia, USA 240 10.0 1 Click here
Whispering Pines 8165 Marsh Point Lane, Black Point Landing, VA, 23336, USA 444 1 Click here
Carriage House 5216 Pine Tree Way, Deep Hole, VA, 23336, USA 516 1 Click here
Island Sunrise - Pet friendly, waterfront duplex! 6423 Pine Drive, Deep Hole, VA, 23336, USA 522 1 Click here
Sunset Dreams - Pet friendly, Waterfront, & shared dock! 3066 Main Street, Black Point Landing, VA, 23336, USA 528 1 Click here
Southern Exposure - Waterfront with boat dock! 7005 Pine Drive, Deep Hole, VA, 23336, USA 529 1 Click here
Sea Oats - Water front with boat dock! 5361 Pearl Drive, Deep Hole, VA, 23336, USA 530 1 Click here
Crabby Pines - Pet friendly modern accommodations! Accomack County 29 10.0 1 Click here
Assateague Inn 104S is an adorable Studio that Accomack County 45 9.34 1 Click here
Les Bon Temps on Chincoteague Island! Accomack County 55 9.72 1 Click here
Fern's Cottage-Renovated,In Town, Perfect Location Accomack County 68 9.54 1 Click here
Eastwinds 18 is a fabulous 2 Bedroom Pet-Friendly Accomack County 70 9.18 1 Click here
Painted Pony Cottage - A short stroll from the Accomack County 75 9.42 1 Click here
Safe Harbor - The Charm you love and the Accomack County 75 9.42 1 Click here
Fishhook Hideaway on Chincoteague Island! Accomack County 75 9.78 1 Click here
Mini Slice of Island Heaven Chincoteague 77 9.54 1 Click here
Private Upstairs at Isle Pines with Waterview Accomack County 80 9.76 1 Click here

Note: The prices for each Landmarks in Chincoteague do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Accommodations in Chincoteague that offer a pool include:

  • Blufin Bungalows & Marina.- Review Count: 205, Rating: 9.6
  • Horseshoe Haven.- Review Count: 1, Rating: 9.0
  • Key West Cottages.- Review Count: 339, Rating: 9.6

Accommodations in Chincoteague with shuttle or transport services include:

  • Chincoteague Bay RV Resort & Cottages.- Review Count: 61, Rating: 9.0

Accommodations in Chincoteague offering spa or wellness facilities include:

  • Horseshoe Haven.- Review Count: 1, Rating: 9.0
  • Quaint Chincoteague Island Hideaway with 2 Porches!.- Review Count: 5, Rating: 7.6

Family-friendly accommodations in Chincoteague include:

  • Channel Bass Inn and Restaurant.- Review Count: 97, Rating: 8.8
  • Blufin Bungalows & Marina.- Review Count: 205, Rating: 9.6
  • Cottage w Private Creek, Sunroom, Fire Pit, & WiFi.- Review Count: 10, Rating: 8.1

Pet-friendly accommodations in Chincoteague include:

  • Channel Bass Inn and Restaurant.- Review Count: 97, Rating: 8.8
  • Blufin Bungalows & Marina.- Review Count: 205, Rating: 9.6
  • Cottage w Private Creek, Sunroom, Fire Pit, & WiFi.- Review Count: 10, Rating: 8.1

Accommodations in Chincoteague that serve free breakfast include:

  • Channel Bass Inn and Restaurant.- Review Count: 97, Rating: 8.8

Accommodations in Chincoteague that offer on-site parking include:

  • Channel Bass Inn and Restaurant.- Review Count: 97, Rating: 8.8
  • Blufin Bungalows & Marina.- Review Count: 205, Rating: 9.6
  • Cottage w Private Creek, Sunroom, Fire Pit, & WiFi.- Review Count: 10, Rating: 8.1

Some of the best Accommodations in Chincoteague are:

  • Channel Bass Inn and Restaurant.- Review Count: 97, Rating: 8.8
  • Cottage w Private Creek, Sunroom, Fire Pit, & WiFi.- Review Count: 10, Rating: 8.1
  • Chincoteague Townhome with Pony Views from Deck!.- Review Count: 9, Rating: 8.4

Some of the popular Accommodations in Chincoteague are:

  • Key West Cottages.- Review Count: 339, Rating: 9.6
  • Blufin Bungalows & Marina.- Review Count: 205, Rating: 9.6
  • Blufin Bungalows & Marina.- Review Count: 111, Rating: 9.2