Best Vacation Rentals in Chesapeake Beach

Top Vacation Rentals in Chesapeake Beach

Plan your perfect getaway with our selection of vacation rentals in Chesapeake Beach. Each choice offers a blend of comfort and local charm, ideal for families and groups.

Vacation Rentals in Chesapeake Beach
Rod 'N' Reel Resort
Resort
4165 Mears Avenue, Chesapeake Beach, MD, MD 20732, USA

Overlooking the Chesapeake Bay, this resort features on-site dining and a full service salon and spa. A gaming room is also on the property. Each guest room at the Rod ’N’ Reel Resort includes a flat-screen cable TV and a refrigerator. Select rooms offer a balcony, water views, a sofa bed, a fireplace or a spa bath. The Rod ’N’ Reel Resort features a seasonal outdoor pool and an indoor pool. A fitness center is also provided. Fishing charters are offered. Rod’N’ Reel offers a waterfront atmosphere while CBQ serves ribs and the outdoor seasonal Boardwalk café serves American cuisine. North Beach is 1.5 mi away from the property.

Guest Reviews:

- "My stay and view was AMAZING!! Me and the fam will b back" - "Delightful" - "Really cute play to stay. Comfortable rooms and pretty views" - "As always we have a Great stay at the Rod n Reel" - "Great place to unwind and relax for a few days!" - "A great hotel in a great location with a wonderful staff." - "The stay was pleasant and very quiet and checked off my comfort level with cleanliness." - "The resort was GORGEOUS and exceptionally CLEAN!! I loved that I could walk into the room and smell that it was cleaned!"

Vacation Rentals in Chesapeake Beach
Rod 'N' Reel Resort
Hotel
4165 Mears Ave, Chesapeake Beach, MD, 20732, USA

Bayside hotel with 2 restaurants and a marina
Along with 2 restaurants, this smoke-free hotel has a marina and an indoor pool. Other amenities include 2 bars/lounges, a 24-hour fitness center, and a snack bar/deli.
Rod 'N' Reel Resort offers 71 air-conditioned accommodations with iPod docking stations and safes. Each accommodation is individually furnished and decorated. Refrigerators and coffee/tea makers are provided. Bathrooms include shower/tub combinations and hair dryers.

Televisions come with cable channels. Business-friendly amenities include desks, desk chairs, and phones. Additionally, rooms include complimentary bottled water and irons/ironing boards. A nightly turndown service is provided and housekeeping is offered daily.


A marina and complimentary bicycles are featured at the hotel. An indoor pool and a seasonal outdoor pool are on site. Other recreational amenities include a sauna and a 24-hour fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Very nice resort hotel. Balcony with a view of the bay. Great location. Close to historic towns to explore. We had a fantastic time!" - "We had an enjoyable stay at this hotel. We celebrated our 21st wedding Anniversary & had dinner down the road & breakfast at the Rod & Reel. Everyone was friendly & easy to work with. Our room had a view of the bay. It was a nice relaxing time away!!" - "Had a wonderful time!!! Relaxing, comfortable facilities!!!Would recommend a stay here to anyone including families of young children. Even though there were babies staying on our floor, we did not hear them when we went to sleep."

Vacation Rentals in Chesapeake Beach
North Beach Cottage - Walk to Chesapeake Bay
House
North Beach, MD, USA

30 miles from Annapolis Harbor in North Beach, North Beach Cottage - Walk to Chesapeake Bay features accommodations with access to a spa center. The air-conditioned accommodation is 28 miles from Addison Road-Seat Pleasant. Free Wifi is available throughout the property and North Beach is a 5-minute walk away. Featuring a patio and garden views, the spacious vacation home includes 3 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 2 bathrooms with a bath and a shower. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Guests can relax in the garden at the property. Ronald Reagan Washington National Airport is 37 miles from the property.

Guest Reviews:

- "Very nice old renovated cottage with all the comforts."

Vacation Rentals in Chesapeake Beach
Sweet Gumball Cottage North Beach MD Free Beach Pass!
House
North Beach, Maryland, USA

Beautiful 2 Queen Bedroom- 1 Bathroom Cottage within walking distance to The Chesapeake Bay Boardwalk and Restaurants! Kick back, Relax and enjoy some quiet time. Fenced in backyard, Covered Patio with ceiling fans as well as uncovered patio to enjoy some outside time. Driveway for parking off street. Cozy & Comfortable. Fully stocked kitchen with stainless steel appliances and granite counter tops. Entertainment room to use as an office, game room or just read or listen to music. Open floor plan living all on 1 floor. TV/ WiFi. Washer/Dryer. Griddle to BBQ. Front Porch Rockers. Quiet Neighborhood.
FREE BEACH PASS for up to 4 People!

Guest Reviews:

- "The property was super nice, equipped with all that was needed and also very organized and clean. The location was perfect, walking distance to the board, restaurants and the beach. The owner was very responsive and flexible. We came as a family to celebrate my birthday and we had a wonderful time! Thank you 💕" - "It was wonderful. Well-appointed decor and art, stocked with ALL the essentials to make your stay comfortable so you're not buying large quantities for short stays (cups, cleaning, laundry, determined-- they went above and beyond. The location Was incredible. Walk to bat, shops, food, and boardwalk — you can even walk to Chesapeake beach. Defiantly would rent again!"

Vacation Rentals in Chesapeake Beach
Waterfront Lux Cottage With Amazing Views Near DC
House
902 Bay Front Avenue, North Beach, MD, MD 20714, USA

Featuring a garden, Waterfront Lux Cottage With Amazing Views Near DC offers accommodations in North Beach. This property offers access to a terrace and free private parking. Annapolis Harbor is 29 miles from the vacation home. With free Wifi, this 1-bedroom vacation home features a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Guests can enjoy a meal on an outdoor dining area while overlooking the sea views. For added privacy, the accommodation features a private entrance. North Beach is 1.2 miles from the vacation home, while Addison Road-Seat Pleasant is 28 miles from the property. Ronald Reagan Washington National Airport is 38 miles away.

Amenities:

Parking • Balcony/Terrace • Barbecue/Outdoor Cooking • Internet • Air Conditioner • View • Child Friendly • Security/Safety

Vacation Rentals in Chesapeake Beach
Unbelievable beach views for 6
Condo
North Beach, Maryland, USA

This beautiful second-floor unit with 2 bedrooms and 1 bathroom is the perfect spot to enjoy a front row seat to stunning Chesapeake Bay sunrises. Sip your morning coffee or afternoon cocktail on the private patio while watching beachgoers below.

Easy access from the free assigned parking spot to the unit, easy access onto the beach, close to restaurants, bars, shopping, activities and more in North Beach and Chesapeake Beach, MD.

Sitting bay front, this second-floor condo is perfect for families with kids (babies through teens), families traveling with grandparents, older guests, girlfriends getaways, romantic getaways and friends trips. This will be your most relaxing, low-stress vacation ever.

Why guests love Bayview House on the Boardwalk:
-Open the balcony door and let the bay breezes blow in
-Wake up to watch the sun rise over the Chesapeake Bay
-Relax and catch your favorite streaming shows in the comfy living room
-Just about everything you need is included in the price you see: linens, bedding, pillows, towels, beach towels
-Guests will have access to 8 FREE beach passes each day (normally $25/each)
-Well-appointed kitchen with everything you need to create delicious meals, beverages, and beach snacks
-Keurig and drip coffee maker available
-Bathroom with a tub-shower combo
-Primary bedroom has a king bed and TV
-A guest room with a comfortable queen bed
-Living room has a sofa-bed (queen size)
-Fantastic location on the boardwalk of North Beach

Bayview House on the Boardwalk is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

This rental is located on floor 2. There is an elevator - perfect for those with mobility limitations and families with young kids (and lots of baby gear).

Parking notes: Assigned parking is available for one vehicle in the spot labeled #35. There is also parking available in the gravel lot on the north side of the building - first-come, first-served.

No pets are allowed at this vacation rental.

You must be 25 years or older to rent this property.

We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit.

For extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.

Guest Reviews:

- "We had a great stay at North Beach. Quiet and relaxing which is what we were looking for. Jen and Mike were great hosts. Communication was excellent. We will be back again soon. " - "Very nice place in a great location!!!" - "This was our 5th trip to North Beach and our 4th time at a condo in Southwinds, and we have never been disappointed. Jenn and Mike, our hosts this time, provided all the information we needed to feel comfortable in their home. We found it exactly as pictured. NB has 5 good restaurants within walking distance and at least 2 more within a 5 minute drive. The boardwalk is great for walking at anytime of day. The new library is a jewel with special sections for all ages and a “makers” room. Teens have a dedicated gaming area. We are now planning our 6th visit!"

Vacation Rentals in Chesapeake Beach
Huge Beach Bungalow- Yard, Beach Pass, King Beds
House
4005 9th Street, North Beach, MD, MD 20714, USA

A 7-minute walk from North Beach in North Beach, Huge Beach Bungalow- Yard, Beach Pass, King Beds provides accommodations with access to a fitness center. This beachfront property offers access to free Wifi and free private parking. Addison Road-Seat Pleasant is 28 miles away and Annapolis Harbor is 29 miles from the vacation home. With direct access to a patio with city views, the spacious air-conditioned vacation home consists of 4 bedrooms. Offering a balcony with garden views, this vacation home also has a satellite flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 3 bathrooms with a walk-in shower and a hair dryer. The property has an outdoor dining area. For guests with children, the vacation home offers an indoor play area and a baby safety gate. Guests at Huge Beach Bungalow- Yard, Beach Pass, King Beds can enjoy fishing and hiking nearby, or make the most of the garden. Ronald Reagan Washington National Airport is 37 miles away.

Amenities:

Air Conditioner • Wellness Facilities • Other • Parking • Ocean View • Pet Friendly • Security/Safety • Guest Services • Breakfast • Child Friendly • Bar • Fireplace/Heating

Vacation Rentals in Chesapeake Beach
Cozy 1st Level Beach House - Walk Everywhere
Apartment
North Beach, Maryland, USA

Summary:
Tucked away in the heart of North Beach, this original 1940s colonial-style home is a delightful blend of modern comfort and rustic-farmhouse warmth. Sunlight seems to find every corner, from the comfortable living room (with ample seating and a TV) into the dining room and country kitchen. Step outside and take summer meals on the spacious, wraparound deck, and linger afterwards in Adirondack chairs around the firepit in the yard.

Your stay is located on the first floor of this duplex-style home, offering a quaint, Chesapeake Bay beach experience.

The Space:
Upon entry, you will immediately fall in love with the home's warm wood flooring and charming beach decor. Any chefs in your group can cook up something delicious in our country-style designed kitchen.

Our living room offers an multiple seating options for families and friends who love to congregate together; especially over a good board game or movie. This is also where guests will find the wall-mounted flat screen television which offers Xfinity cable service with hundreds of local and national network options, a DVD/ Blu-Ray player (with a small library of movies), and Roku Streaming Entertainment Service. We also provide two sofa chairs that pull out to offer additional sleeping options for larger group reservations.

All of our bedrooms, bathroom, and washer/dryer area all available on the main floor. Guests will find our bathroom fully stocked with towels and an assortment of bath amenities available for use.

For sleeping arrangements, guests have access to our a primary bedroom with a King-sized bed as well as a jack-and-jill style bedroom with Queen Bed and a beautiful wooden bunk bed (that can accommodate two adults or children utilizing both the bottom and top bunks). There is also an additional sleeper sofa in the living room for guests who need to host a larger group.

Outside, you will have shared access to a spacious deck, outdoor seating and charcoal grill.

Guest Access:
Guests are provided with private access and use of the entire 1st floor, a fully furnished home that we actively update and maintain on an ongoing basis.

As a 2-unit vacation rental house, there are a small number of shared amenities available to all guests on a first come, first serve basis. We always encourage guests to coordinate with each other if they have a desire to use any of the shared features during a specific day or timeframe. We've yet to have a conflict that wasn't easily reconciled to the benefit of both guests.

The first of these shared accommodations is the off-street driveway parking. The gravel driveway sits on the right side of the house (when facing the house from the street), and is wide enough for a single vehicle, however does provide plenty of length for 2 larger vehicles to park nose to tail without obstructing the street or sidewalk. With that in mind, we ask any guests whose party arrives in 2+ vehicles that choose to park in the driveway to make an effort to take full advantage of the 2 driveway spaces with 2 vehicles. While on-street parking is rarely an issue, it can become crowded at times for other guests and our neighbors without driveways, and every little bit counts.

The house features a wrap-around deck and an outdoor table, chair, and umbrella set for shared use. We provide a propoane/charcoal grill as well. The grill is not large enough for more than one grill-master at a time, so we encourage guests to coordinate with each other for any planned use of these amenities.

For all of the TVs in the home, you can use your own streaming accounts to enjoy your favorite shows and movies. The vacation rental does not include access to any paid streaming services unless Guests use their account credentials. However, we do provide guests with a basic cable package, which provides a limited number of standard definition (SD) and High Definition (HD) cable television options.

The Neighborhood:
Nearby, you'll be just minutes from beaches, bakeries, and breweries. North Beach offers a great mix of antique stores, gardens, gift stores, ice cream shops, and of course, the North Beach Boardwalk. While access to the boardwalk is open to the general public, the beach itself requires a pass between Memorial Day and Labor Day. Two residential passes (good for up to eight guests) are provided in the home. The cost to access the beach without a pass is $25 per person/per day. Additionally, a variety of beach gear is provided to guests including towels, chairs, a wagon, umbrella, and cooler - all are available on a first-come, first-served basis. Additional beach gear is available for rent at the beach should you need anything else for your visit.

Many fellow residents living in the area of North Beach regularly use our street during their daily pilgrimage to the water. This has the benefit of providing residents living on our little section of 3rd Street with a disproportionately high level of human diversity than one would normally expect for an area of this small size. This anomaly is both welcomed with open arms and appreciated by our neighbors.

The location puts Guests less than a mile walk to the North Beach boardwalk, pier, public beach, coffee shops, antique shops, US Post Office, and ice cream shops.

There is always something going on in North Beach, regardless of time of the year. We'll do our best to keep you posted about what is planned during your stay, and make sure you are provided with the resources to find more information.

Getting Around:
The home's proximity to the Chesapeake Bay means the boardwalk, beaches, and majority of shops & restaurants in North Beach are just a short 10 minute walk away.

The public transportation options are limited, but the county does operate a regularly scheduled bus route during weekdays, as well as limited service on weekends.

Interaction with Guests:
We have a property manager who lives in/near Annapolis. He is approximately 30-45 min drive away from you and can assist in an emergency situation.

Amenities:

Child Friendly • Other • Tv • Barbecue/Outdoor Cooking • View • Security/Safety • Ocean View • Parking • Fireplace/Heating • Laundry • Oceanfront • Kitchen

Vacation Rentals in Chesapeake Beach
Cozy 1st Level Beach House - Walk Everywhere
Apartment
3rd Street 3940, North Beach, MD, 20714-4053, USA

Cozy 1st Level Beach House - Walk Everywhere offers accommodations in North Beach, a 4-minute walk from North Beach and 29 miles from Addison Road-Seat Pleasant. This apartment features air-conditioned accommodations with a patio. Outdoor seating is also available at the apartment. With free Wifi, this 2-bedroom apartment provides a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the apartment. The accommodation has a fireplace. Guests can also relax in the garden. Annapolis Harbor is 29 miles from Cozy 1st Level Beach House - Walk Everywhere. Ronald Reagan Washington National Airport is 37 miles away.

Amenities:

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

Vacation Rentals in Chesapeake Beach
Charming Beach House Top Floor - Walk Everywhere!
Apartment
North Beach, Maryland, USA

Summary:
Tucked away in the heart of North Beach, this original 1940s colonial-style home comes fully restored! Up a flight of stairs, your stay is located on the second story of this duplex-style home, offering a quaint, Chesapeake Bay beach experience.

The space has an open floor plan with 14' cathedral ceilings for a grand feel but with beach-house charm. Only a 2 block walk to the beach and boardwalk!

Guests who do not handle stairs well should engage us before making a reservation. We would love to offer you the downstairs space first or set transparent expectations for you if you proceed with a reservation.

The Space:
Upon entry, you will immediately fall in love with the home's cathedral ceilings, warm wood flooring, and open layout. Any chefs in your group can cook up something delicious with the help of our stainless steel appliances, full-sized Samsung French door refrigerator with a bottom pull-out freezer drawer, electric smooth-top 4 burner stove and broiler-capable oven.

Our living room offers an oversized sofa perfect for families and friends who love to congregate together; especially over a meal. This is also where guests will find the wall-mounted flat screen television which offers Xfinity cable service with hundreds of local and national network options, a DVD/ Blu-Ray player (with a small library of movies), and Roku Streaming Entertainment Service. We also provide two sofa chairs that pull out to offer additional sleeping options for larger group reservations.

There is a bedroom, bathroom, and washer/dryer area all available on the main floor. In the bathroom, you'll find a newly refinished cast iron clawfoot bathtub; equipped for quick showers as well. Guests will find our bathroom fully stocked with towels and an assortment of bath amenities available for use.

Up an additional set of stairs, the loft offers an additional king-sized bed, one full-sized bed, and one twin bed. There is also a small seating area with a TV, board games, and plenty of storage options for unpacking your personal items. The stairs to the loft are at a steeper pitch than a normal staircase, so please use caution and ensure the space suits your needs.

Outside, you will have shared access to a spacious deck, outdoor seating and charcoal grill.

Guest Access:
Guests are provided with private access and use of the entire 2nd floor, a fully furnished home that we actively update and maintain on an ongoing basis.

As a 2-unit vacation rental house, there are a small number of shared amenities available to all guests on a first come, first serve basis. We always encourage guests to coordinate with each other if they have a desire to use any of the shared features during a specific day or timeframe. We've yet to have a conflict that wasn't easily reconciled to the benefit of both guests.

The first of these shared accommodations is the off-street driveway parking. The gravel driveway sits on the right side of the house (when facing the house from the street), and is wide enough for a single vehicle, however does provide plenty of length for 2 larger vehicles to park nose to tail without obstructing the street or sidewalk. With that in mind, we ask any guests whose party arrives in 2+ vehicles that choose to park in the driveway to make an effort to take full advantage of the 2 driveway spaces with 2 vehicles. While on-street parking is rarely an issue, it can become crowded at times for other guests and our neighbors without driveways, and every little bit counts.

The house features a wrap-around deck and an outdoor table, chair, and umbrella set for shared use. We provide a propane/charcoal grill as well. The grill is not large enough for more than one grill-master at a time, so we encourage guests to coordinate with each other for any planned use of these amenities.

For all of the TVs in the home, you can use your own streaming accounts to enjoy your favorite shows and movies. The vacation rental does not include access to any paid streaming services unless Guests use their account credentials. However, we do provide guests with a basic cable package, which provides a limited number of standard definition (SD) and High Definition (HD) cable television options.

The Neighborhood:
Nearby, you'll be just minutes from beaches, bakeries, and breweries. North Beach offers a great mix of antique stores, gardens, gift stores, ice cream shops, and of course, the North Beach Boardwalk. While access to the boardwalk is open to the general public, the beach itself requires a pass between Memorial Day and Labor Day. Two residential passes (good for up to eight guests) are provided in the home. The cost to access the beach without a pass is $25 per person/per day. Additionally, a variety of beach gear is provided to guests including towels, chairs, a wagon, umbrella, and cooler - all are available on a first-come, first-served basis. Additional beach gear is available for rent at the beach should you need anything else for your visit.

Many fellow residents living in the area of North Beach regularly use our street during their daily pilgrimage to the water. This has the benefit of providing residents living on our little section of 3rd Street with a disproportionately high level of human diversity than one would normally expect for an area of this small size. This anomaly is both welcomed with open arms and appreciated by our neighbors.

The location puts Guests less than a mile walk to the North Beach boardwalk, pier, public beach, coffee shops, antique shops, US Post Office, and ice cream shops.

There is always something going on in North Beach, regardless of time of the year. We'll do our best to keep you posted about what is planned during your stay, and make sure you are provided with the resources to find more information.

Getting Around:
The home's proximity to the Chesapeake Bay means the boardwalk, beaches, and majority of shops & restaurants in North Beach are just a short 10 minute walk away.

The public transportation options are limited, but the county does operate a regularly scheduled bus route during weekdays, as well as limited service on weekends.

Interaction with Guests:
We have a property manager who lives in/near Annapolis. He is approximately 30-45 min drive away from you and can assist in an emergency situation.

Amenities:

View • Oceanfront • Fireplace/Heating • Other • Air Conditioner • Laundry • Bedding/Linens • Tv • Barbecue/Outdoor Cooking • Wellness Facilities • Parking • Sports/Activities

Vacation Rentals in Chesapeake Beach
Coastal Pet-Friendly Cottage Less Than half Mi to Beaches
House
Chesapeake Beach, MD, USA

Coastal Pet-Friendly Cottage Less Than half Mi to Beaches offers accommodations in Chesapeake Beach, a 13-minute walk from North Beach and 28 miles from Addison Road-Seat Pleasant. This beachfront property offers access to free Wifi. Annapolis Harbor is 29 miles from the vacation home. Providing a patio and sea views, the spacious vacation home includes 2 bedrooms, a living room, flat-screen TV, an equipped kitchen, and 1 bathroom with a shower. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Ronald Reagan Washington National Airport is 37 miles away.

Amenities:

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

Vacation Rentals in Chesapeake Beach
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
House
North Beach, Maryland, USA

Modern three-bedroom, two full bath home with half-bath and new furnishings. Quiet neighborhood easily accessible to Saturday Farmer's Market , Chesapeake boardwalk & beach, restaurants, ice cream shops, water park, charter fishing, water crafts and casino. Complete well-stocked kitchen perfect for dining in or eating a quick snack.

Soaking tub in master bath with a free-standing shower, dining table seats 8, breakfast table, open floor plan with cozy reading/computer room, great porch with rockers to relax and enjoy your morning coffee or an evening glass of your favorite beverage. Deck with table & umbrella and seating for 6, plus Weber 3-burner propane grill for outdoor cooking. Grill tools furnished. Large flat back yard for kids (large or small) to play.

Plenty to do and only a short distance from Annapolis, Washington DC, Northern Virginia, or Baltimore. Explore all Calvert Country has to offer with plenty of parks and play grounds. Extremely kid-friendly - tot-sized plates &utensils, books galore, games & puzzles for all ages, building blocks and outdoor games. Pack n play, two baby-gates for stairs. Bunk-bed room with toys, books and bean bag chairs is a kiddo favorite.

Guest Reviews:

- "We appreciated the amenities, games, spacious living areas, air conditioning, and cleanliness. We enjoyed being able to walk to restaurants and the boardwalk. Thank you for the memorable stay." - "This property was perfect for our 1 week stay. Extremely clean, spacious, very well appointed. Close to boardwalk, playground, beach, restaurants, ice cream shop. Our host was extremely helpful, flexible and communicated in a very timely fashion. We had a wonderful family vacation!"

Vacation Rentals in Chesapeake Beach
Charming Beach House Top Floor - Walk Everywhere
Apartment
3rd Street, North Beach, MD, 20714, USA

Charming Beach House Top Floor - Walk Everywhere offers accommodations in North Beach, a 4-minute walk from North Beach and 29 miles from Addison Road-Seat Pleasant. This apartment provides air-conditioned accommodations with a patio. Outdoor seating is also available at the apartment. With free Wifi, this 2-bedroom apartment offers a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the apartment. For added privacy, the accommodation features a private entrance. Guests can also relax in the garden. Annapolis Harbor is 29 miles from Charming Beach House Top Floor - Walk Everywhere. Ronald Reagan Washington National Airport is 37 miles away.

Amenities:

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

Vacation Rentals in Chesapeake Beach
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
House
Chesapeake Beach, Maryland, USA

Come enjoy living in mid-century modern style, with sweeping views of the Chesapeake Bay, all within a short drive from the Washington, DC metropolitan area, Annapolis, Solomons Island, fishing charters and our many local historic sites. This property is also U.S. Army veteran (Afghanistan and Iraq) owned and operated, as well as LGBTQ safe and friendly.

Award winning local architect, James William Ritter III, of Ritter-Norton Architecture, located in Alexandria, Virginia, purchased, completely rebuilt and redesigned this home for his wife and himself, when they began their retirement. The architect's son, Mark Ritter, and his spouse, Nicholas Knowlton, now own the home and want to welcome you to enjoy this unique house and its magical setting. https://www.ritternorton.com/james

Here, you'll enjoy the true modern ideal of blurring the lines between interior and exterior spaces. Wake up in the morning to the sounds of seabirds calling and waves lapping on the beach. Start your day right, in our open, multi-head, shower stall, with heated floors and protected views of our perennial garden. A huge bank of windows and sliding glass doors makes the Bay the centerpiece of the entire living and kitchen areas. The house draws you outside to enjoy a morning cup of coffee on the veranda, head down the stairs for direct access to a day on the beach or simply enjoy a glass of wine, while relaxing with a book in the hammock.

Disclosure: We have hard water. Most of our renters had no complaints or issues, but it has bothered one or two. Therefore, we decided to be upfront about it, rather than have a renter find out upon arrival. Hard water is a problem you’ll unfortunately find in almost any home in this region. We do not provide refunds relating to this issue, given this upfront disclosure.

Guest Reviews:

- "This property is BEAUTIFUL! We could not believe the views, I practically lived in that hammock. The only downside was the bay was filled with Jellyfish, so we could not swim. That’s just nature I guess. I would LOVE to stay here again." - "It really was the recharge refuge that me and my friend needed. Beautiful and unique spot. The tap water smells a bit of sulfur. The path down to the beach is a little rough after a rain. But those are small quibbles with an overall lovely place."

Vacation Rentals in Chesapeake Beach
Family-Friendly Chesapeake Beach House with Deck!
House
Chesapeake Beach, MD, USA

Free Wifi is available throughout the property and Addison Road-Seat Pleasant is 30 miles away. The spacious vacation home includes 1 bedroom, a fully equipped kitchen with an oven and a microwave, as well as a coffee machine. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. Ronald Reagan Washington National Airport is 39 miles away.

Guest Reviews:

- "Great place for a party of 6."

Vacation Rentals in Chesapeake Beach
The Blue Crab Beach House - Free beach passes
House
North Beach, Maryland, USA

Welcome to The Blue Crab just a few blocks from the Chesapeake Bay. You will enjoy staying at our newly renovated luxury cottage. We are located on the very popular 7th Street where you can walk to the beach, a variety of restaurants, and shops. We have FREE beach passes for up to 4 guests.

Featuring a fully fenced yard, our beach cottage is the perfect choice for families who want to bring their dog/s along for the fun. With a beach theme throughout, our rental is the perfect place to relax and unwind after a day at the beach.
In the family room, you'll find a comfortable surround couch and a cozy fireplace, perfect for relaxing on cool nights. The fully fenced backyard features a deck - proving the perfect spot for outdoor dining and even star gazing. Featuring a complete laundry room with a washer and dryer, you won't have to worry about running out of clean clothes during your stay. Also, choose off street or on street parking - whichever you prefer.

We provide all linens, beach chairs, an umbrella and beach towels, making it easy for you to pack light and enjoy your vacation to the fullest. And with a safe, friendly neighborhood that takes pride in its surroundings, you'll feel right at home during your stay.

Need more room? The Lazy Crab is now open - just next door!

Guest Reviews:

- "We didn’t realize how many short steps there were between rooms, which was an issue for one of our guests. We suggest that you add some nightlights or mark those steps. Overall, the experience was excellent. The rooms were very clean and artfully decorated. Follow up to make certain we didn’t need anything was much appreciated." - "We really enjoyed the area and the rental home. Everything was lovely." - "My mini doodle and I stayed in this charming and cozy cottage just blocks from great restaurants, coffee shop, retail and the beach. The property is totally fenced in! The house has all the amenities you need. North Beach is a friendly charming community. Thank you Danielle for a lovely stay. We will be back!"

Vacation Rentals in Chesapeake Beach
Adorable Beach Cottage with Hot Tub and Tropical Bar!
House
Chesapeake Beach, MD, USA

30 miles from Addison Road-Seat Pleasant in Chesapeake Beach, Adorable Beach Cottage with Hot Tub and Tropical Bar! offers accommodations with access to a hot tub. This vacation home features air-conditioned accommodations with a patio and free Wifi. Featuring a balcony and sea views, the vacation home includes 2 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 1 bathroom with a hot tub and a bath. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. There is an on-site bar. Ronald Reagan Washington National Airport is 39 miles from the property.

Guest Reviews:

- "This cottage is beautiful. Very well designed with great use of space." - "We would definitely book again!"

Vacation Rentals in Chesapeake Beach
Blocks to the Boardwalk!
House
North Beach, Maryland, USA

Park right in front of this beautiful cottage enclosed with a white picket fence.
Everything is in walking distance from The Bee. The town stretches over seven blocks of waterfront, with a popular fishing pier and a long boardwalk. The boardwalk has a separate bike path and is lined with benches that are perfect for relaxing and enjoying the view of Chesapeake Bay. There is a fee for using both the beach and the fishing pier for non- residents. But we have beach passes included for our guests plus beach chairs, umbrella and wagon. Paddleboards, kayaks, and bikes are available for rent at the beach.
The town’s gift, antique shops, and restaurants are walking distance from the beach, should you have had enough of the sun. From May to October there is a popular Saturday morning farmers market.
Our tiny house perfect for a romantic getaway for just two, a small family, or a group of friends.
The Bee by the Bay has a fenced yard for your family and pets to play safe and securely. Veteran owned business.

Guest Reviews:

- "North Beach was just what we wanted. Quiet, walkable and friendly. The walk to the beach was very doable especially with the wagon to carry beach chairs and umbrella all provided by the host. A beach pass was also provided. The kitchen was well stocked and both the futon and bed mattress were comfortable. Lots of outdoor sitting space. We would definitely return." - "Great location three blocks from the beach! Very dog friendly town with plenty of restaurants and a beautiful mile and a half boardwalk. The “Bee” is a beautiful, well stocked, cottage with plenty of room for 2-3 people and their dogs. A fenced in backyard is perfect!!"

Vacation Rentals in Chesapeake Beach
1 Mi to Boardwalk Convenient North Beach Apt!
Apartment
North Beach, MD, USA

1 Mi to Boardwalk Convenient North Beach Apt! is located in North Beach, just 1.3 miles from North Beach and 28 miles from Addison Road-Seat Pleasant. Free Wifi is provided throughout the property and private parking is available on site. The apartment features 1 bedroom, a fully equipped kitchen with a microwave and a toaster, a washing machine, and 1 bathroom with free toiletries. Towels and bed linen are featured in the apartment. For added privacy, the accommodation features a private entrance. Annapolis Harbor is 29 miles from 1 Mi to Boardwalk Convenient North Beach Apt!. Ronald Reagan Washington National Airport is 37 miles away.

Guest Reviews:

- "Well worth it, definitely coming back!" - "Great location, lovely place with everything that we needed" - "Nice place, very clean and a cute town." - "Nice basement to relax and sleep."

Vacation Rentals in Chesapeake Beach
Waterfront North Beach Home ~ 2 Mi to Beach!
House
North Beach, Maryland, USA

Highlighted by its coastal charm and scenic location, this well-appointed North Beach home is well-suited for small groups to enjoy a relaxing stay on Chesapeake Bay. This 2-bedroom, 2-bathroom vacation rental features Smart TVs, free WiFi, a screened porch with a convertible dining table and pool table, and a large fenced yard for your furry friend. After a sunny day spent relaxing at the beach or exploring town attractions, you can gather around the fire pit to unwind under the stars.

-- THE PROPERTY --

Anne Arundel County STR Reg: STR-00460 | Pet Friendly w/ Fee | View of Chesapeake Bay | 2 Mi to North Beach Town

Bedroom 1: Queen Bed | Bedroom 2: Queen Murphy Bed | Loft: King Bed

INDOOR LIVING: Smart TVs, sunroom w/ sitting area, laptop-friendly work area, cable/satellite TV
OUTDOOR LIVING: Screened porch w/ outdoor dining area & convertible pool table, solo stove fire pit, charcoal grill, 2 kayaks, fenced yard, patio, walk to Rose Haven Memorial Park
KITCHEN: Cooking basics, dishware/flatware, dishwasher, stove/oven, microwave, coffee maker, coffee grinder, blender, toaster oven, spices
GENERAL: Free WiFi, linens/towels, complimentary toiletries, washer/dryer, ceiling fans, window A/C units, hair dryer, laundry detergent, trash bags/paper towels
FAQ: 3 steps required to access, 1 exterior security camera (outward facing), pet fee (paid pre-trip)
PARKING: Driveway (4 vehicles)

-- THE LOCATION --

BEACHES: North Beach Boardwalk/Beach (2.3 miles), Chesapeake Beach Veterans Memorial Park (2.9 miles), Brownie’s Beach (4.2 miles), Bayfront Beach (4.4 miles), Breezy Point Beach (9.2 miles)
OUTDOOR RECREATION: Rose Have Memorial Park (190 ft), Herrington Harbor Yacht Club (0.3 miles), Tyler’s Tackle Shop & Crab House (2.9 miles), Reel Attitude Charters (3.3 miles), Katherine Charter Fishing (3.3 miles), Fishing Creek Chesapeake Beach Maryland (3.3 miles), Chesapeake Beach Fishing (3.4 miles), Chesapeake Adventures Sportfishing (21.5 miles)
ATTRACTIONS: Chesapeake Beach Water Park (3.1 miles), Chesapeake Beach Railway Museum (3.4 miles), Jug Bay Wetlands Sanctuary (14.2 miles), Six Flags America (23.6 miles)
NEARBY EATS: Traders Seafood Steak & Ale (3.0 miles), Abners Crab House (3.3 miles), Rod ‘N’ Reel Restaurant (3.4 miles), Boardwalk Cafe (3.4 miles)
WASHINGTON D.C. (~36 miles): United States Capitol, The White House, Lincoln Memorial, National Mall, Smithsonian National Air and Space Museum, attractions, sightseeing, events, nightlife, restaurants
AIRPORTS: Ronald Reagan Washington National Airport (36.4 miles), Baltimore/Washington International Thurgood Marshall Airport (45.0 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
- Pet friendly w/ $75 fee (+ fees and taxes)
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The property requires 3 steps to access
- NOTE: Your safety matters. This property features 1 exterior security camera. The camera is a Ring doorbell located on the front entry. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion

Guest Reviews:

- "We had a wonderful week long stay at this house. Looked just like the pictures, proximity to the ocean was wonderful (we walked down to the water every night with our son and dog) and a quick 5 minutes drive into North Beach, which had a beautiful, very kid friendly beach, a good grocery store, coffee shop, ice cream shop, and a range of restaurants. The house was very dog friendly - a couple dog beds, a bunch of bowls and a very secure back yard. House also worked well with our toddler, the small office room was perfect for him. Just a quick flag, the only table to eat on was the covered pool table on the screened in porch. Not an issue for us as it was summer and we loved eating outside every night, but could be less comfortable when it's chillier out. We will definitely stay in the house again on our next visit to North Beach!"

Chesapeake Beach Family Friendly Vacation rentals

Chesapeake Beach Vacation rentals with Parking

Chesapeake Beach Pet Friendly Vacation rentals

Chesapeake Beach Vacation rentals with Entertainment

Chesapeake Beach Vacation rentals with Spa

Chesapeake Beach Vacation rentals with Private Pool

Chesapeake Beach Vacation rentals with Private Beach

Chesapeake Beach Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in Chesapeake Beach – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Rod 'N' Reel Resort 4165 Mears Avenue, Chesapeake Beach, MD, MD 20732, USA 422 4.0 8.0 420 Click here
Rod 'N' Reel Resort 4165 Mears Ave, Chesapeake Beach, MD, 20732, USA 132 4.0 8.4 1003 Click here
North Beach Cottage - Walk to Chesapeake Bay North Beach, MD, USA 290 4.0 10.0 4 Click here
Sweet Gumball Cottage North Beach MD Free Beach Pass! North Beach, Maryland, USA 199 2.0 10.0 14 Click here
Waterfront Lux Cottage With Amazing Views Near DC 902 Bay Front Avenue, North Beach, MD, MD 20714, USA 190 4.0 9.0 2 Click here
Unbelievable beach views for 6 North Beach, Maryland, USA 273 2.0 10.0 9 Click here
Huge Beach Bungalow- Yard, Beach Pass, King Beds 4005 9th Street, North Beach, MD, MD 20714, USA 494 4.0 10.0 2 Click here
Cozy 1st Level Beach House - Walk Everywhere North Beach, Maryland, USA 354 2.0 1 Click here
Cozy 1st Level Beach House - Walk Everywhere 3rd Street 3940, North Beach, MD, 20714-4053, USA 183 4.0 1 Click here
Charming Beach House Top Floor - Walk Everywhere! North Beach, Maryland, USA 382 2.0 1 Click here
Coastal Pet-Friendly Cottage Less Than half Mi to Beaches Chesapeake Beach, MD, USA 222 4.0 1 Click here
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants. North Beach, Maryland, USA 286 10.0 100 Click here
Charming Beach House Top Floor - Walk Everywhere 3rd Street, North Beach, MD, 20714, USA 366 4.0 1 Click here
Mid-Century Modern on Private Beach, Designed by Award Winning Architect! Chesapeake Beach, Maryland, USA 289 10.0 84 Click here
Family-Friendly Chesapeake Beach House with Deck! Chesapeake Beach, MD, USA 187 3.0 8.8 4 Click here
The Blue Crab Beach House - Free beach passes North Beach, Maryland, USA 210 10.0 76 Click here
Adorable Beach Cottage with Hot Tub and Tropical Bar! Chesapeake Beach, MD, USA 218 3.0 9.3 4 Click here
Blocks to the Boardwalk! North Beach, Maryland, USA 157 9.8 44 Click here
1 Mi to Boardwalk Convenient North Beach Apt! North Beach, MD, USA 228 3.0 9.0 3 Click here
Waterfront North Beach Home ~ 2 Mi to Beach! North Beach, Maryland, USA 367 10.0 27 Click here

Note: The prices for each Vacation-Rentals in Chesapeake Beach 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

Vacation rentals in Chesapeake Beach that include a pool include:

  • Rod 'N' Reel Resort.- Review Count: 420, Rating: 8.0
  • Rod 'N' Reel Resort.- Review Count: 1003, Rating: 8.4

These vacation rentals in Chesapeake Beach provide spa or wellness access:

  • Rod 'N' Reel Resort.- Review Count: 1003, Rating: 8.4
  • North Beach Cottage - Walk to Chesapeake Bay.- Review Count: 4, Rating: 10.0
  • Updated North Beach Cottage Pet Friendly!.- Review Count: 2, Rating: 9.5

Family-friendly vacation rentals in Chesapeake Beach include:

  • Rod 'N' Reel Resort.- Review Count: 420, Rating: 8.0
  • Rod 'N' Reel Resort.- Review Count: 1003, Rating: 8.4
  • North Beach Cottage - Walk to Chesapeake Bay.- Review Count: 4, Rating: 10.0

Pet-friendly vacation rentals in Chesapeake Beach include:

  • Huge Beach Bungalow- Yard, Beach Pass, King Beds.- Review Count: 2, Rating: 10.0
  • Cozy 1st Level Beach House - Walk Everywhere.- Review Count: 0, Rating: 0.0
  • Cozy 1st Level Beach House - Walk Everywhere.- Review Count: 0, Rating: 0.0

Vacation rentals in Chesapeake Beach that include breakfast options include:

  • Rod 'N' Reel Resort.- Review Count: 1003, Rating: 8.4
  • Huge Beach Bungalow- Yard, Beach Pass, King Beds.- Review Count: 2, Rating: 10.0

Vacation rentals in Chesapeake Beach with private or on-site parking include:

  • Rod 'N' Reel Resort.- Review Count: 420, Rating: 8.0
  • North Beach Cottage - Walk to Chesapeake Bay.- Review Count: 4, Rating: 10.0
  • Sweet Gumball Cottage North Beach MD Free Beach Pass!.- Review Count: 14, Rating: 10.0

Some of the best Vacation Rentals in Chesapeake Beach are:

  • Rod 'N' Reel Resort.- Review Count: 1003, Rating: 8.4
  • Rod 'N' Reel Resort.- Review Count: 420, Rating: 8.0
  • North Beach Cottage - Walk to Chesapeake Bay.- Review Count: 4, Rating: 10.0

Some of the popular Vacation Rentals in Chesapeake Beach are:

  • Rod 'N' Reel Resort.- Review Count: 1003, Rating: 8.4
  • Rod 'N' Reel Resort.- Review Count: 420, Rating: 8.0
  • Spacious house, great deck & grill, close to boardwalk, shops, and restaurants..- Review Count: 100, Rating: 10.0