Explore Top Vacation Rentals in Southold, NY

Located in Southold, 23 miles from Splish Splash, The Shoals Suites & Slips provides accommodations with a garden, free private parking, a terrace and a bar. This 4-star hotel has air-conditioned rooms with a private bathroom. Free WiFi and a concierge service are featured. All guest rooms will provide guests with a fridge. The hotel also provides a business center and guests can use the on-site ATM machine at The Shoals Suites & Slips. Long Island Railroad is 14 miles from the accommodation. Long Island MacArthur Airport is 45 miles away.

Internet • Sports/Activities • Parking • Air Conditioner • Guest Services • Other • View • Balcony/Terrace • Security/Safety • Business Services • Fireplace/Heating • Bar

Bayside hotel with a coffee shop and a bar
This smoke-free hotel features a bar/lounge, a coffee shop/cafe, and a business center. Additionally, free use of bicycles, concierge services, and a computer station are onsite.
Housekeeping is available on request.
The Shoals Suites and Slips offers 20 air-conditioned accommodations with espresso makers and bathrobes. Rooms open to furnished balconies or patios. These individually decorated and furnished accommodations have separate sitting areas. Beds feature down comforters and premium bedding. A pillow menu is available. 43-inch flat-screen televisions come with Netflix.

Bathrooms include showers with rainfall showerheads, and hair dryers. This Southold hotel provides complimentary wireless Internet access, with a speed of 50+ Mbps. Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided daily.

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

- "Great stay!" - "Nice, comfy, and stylish " - "The room was beautiful and what a view! We will definitely be back!" - "It was a cute and lovely place and I really impressed by the smiles and attitudes of the staff " - "The count staff was very friendly and clean and all the facilities were comfortable and nice." - "Check in was quick and the young lady at the front desk was super friendly. I had sent a message prior to my visit with a small request and the reason why. When we got to our room, not only did they honor my request, but there was a very sweet surprise waiting for us! So thoughtful and definitely above and beyond. The room itself was so beautifully decorated and well thought out. It had a naturally comfortable feel while being a step above the norm. There is an area at check-in that has provisions like snacks and adult beverages while also offering clothing, jewelry and gifts. I absolutely loved the sitting area off the lobby. Such a well designed and beautifully decorated space. It's the type of area you would just love to spend time in. The views of the port, and the water were just fantastic. If this hotel was this impressive off season, I would absolutely choose this property for a vacation during the summer. The Shoals is little hidden gem, trust me. "

Classic Southold Country Charmer offers accommodations in Southold, 21 miles from Splish Splash. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. Offering a patio, this vacation home also features a satellite flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 1 bathroom with a walk-in shower and a hair dryer. The property has an outdoor dining area. Long Island MacArthur Airport is 43 miles from the property.

Fireplace/Heating • Barbecue/Outdoor Cooking • Accessibility • Balcony/Terrace • Restaurant • View • Wheelchair Accessible • Child Friendly • Security/Safety • Laundry • Sports/Activities

Beach bed & breakfast with a nearby private beach and free breakfast
Start your day with a complimentary full breakfast, then head to Shorecrest Bed and Breakfast's private beach where you can enjoy kayaking.
Shorecrest Bed and Breakfast offers 5 air-conditioned accommodations with complimentary toiletries. Each accommodation is individually furnished. Beds feature premium bedding. Flat-screen televisions come with satellite channels. This Southold bed & breakfast provides complimentary wireless Internet access. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "Excellent amenities, great service, and wonderful location! " - "BEautiful place, with friendly and accomodating inn keeper, with extremely clean and comfortable accomodations." - "When you think of a beautiful bed & breakfast...this is it ,inside & out. A lot attention to detail. Breakfast was presented beautifully and was delicious. Across the street was a private small beach, perfect for peaceful time." - "We had a beautiful experience. The owner was just amazing, breakfast was delicious."

Bright Oasis in Beautiful North Fork Wine Country offers accommodations in Southold, 21 miles from Splish Splash. There's an outdoor fireplace and guests can use free Wifi and free private parking. Providing access to a patio with garden views, the spacious air-conditioned vacation home consists of 4 bedrooms. Offering a terrace with river views, this vacation home also features a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a walk-in shower and a hair dryer. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Southold, like canoeing. A baby safety gate is also available at Bright Oasis in Beautiful North Fork Wine Country, while guests can also relax in the garden. Long Island MacArthur Airport is 43 miles from the property.

Fireplace/Heating • Balcony/Terrace • Parking • View • Other • Internet • Oceanfront • Air Conditioner • Child Friendly • Security/Safety • Pet Friendly • Sports/Activities

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. A 20 minute drive from the Orient Point Ferry Terminal.

*IMPORTANT*

Seasonal items like the grill are only available from May 1st to October 31st.

- "Our stay at Mae’s house was everything we could have ever wanted. Her home and property are gorgeous! Mae was very responsive and so pleasant to deal with. Everything was perfect and as described! What you see is what you get and so much more! We had a wonderful time and will definitely be back and are already counting the days!" - "Spent a week in this lovely cottage that was the perfect size for the three of us. The cottage is quaint and private and is surrounded by the inlet and land preserve so while neighbors are nearby, they are not on top of you. Backyard was relaxing and took advantage of the hammock nestled in between trees. Kayaks were a plus and many launches on the inlet gets you up close to the many birds living around the inlet (not often you are within a few feet of Osprey hunting!). Beach was a short walk away and took advantage on hot days. The house is the prefect location as it is close to many hikes, towns, shops, and vineyards to explore. Never more than a 20 minute drive to exploring the whole region. Mae was such a responsive and lovely host and appreciated her help when needed. Only wish was that the primary bed was a Queen or King size to accommodate two larger people comfortably. Regardless, I hope to be able to come back and rent again! Thanks for a great stay!"

Minnehaha Marvel offers accommodations in Southold, 21 miles from Splish Splash. The vacation home has access to a restaurant. Outdoor seating is also available at the vacation home. The air-conditioned vacation home consists of 1 bedroom, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are offered in the vacation home. There's also a seating area and a fireplace. Long Island MacArthur Airport is 43 miles from the property.

Private Beach • Laundry • Restaurant • Guest Services • Ocean View • Barbecue/Outdoor Cooking • Pet Friendly • Balcony/Terrace • Air Conditioner • Fireplace/Heating • Sports/Activities • Security/Safety

Welcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New York has to offer!

And welcome to our home: a fully-renovated, brand new everything stylish retreat located in Southold—just minutes from Goose Creek Beach, North Fork Roasting Company, Southold Fish Market and Corey Creek Winery.

Every inch of the house and its furnishings are brand new. It features tons of natural light via vaulted ceilings and multiple skylights throughout the living, family and kitchen areas. With an open concept, this property offers the perfect space for families looking to entertain, dine, grill and enjoy the peacefulness of this cul-de-sac property.

The house has been curated with love and we hope you enjoy it as much as we do!

Amenities include, but are not limited to:
- 4 bedrooms (1 king, 2 queens, 2 twins)
- 2 full bathrooms
- propane gas grill
- firepit
- Adirondack chairs
- outdoor shower
- outdoor dining room
- outdoor lounge area
- smart TVs (70' and 55') with Netflix, Hulu, Amazon, etc.
- Google Home
- washer & dryer
- Wifi included
- concierge garbage pick-up
- queen blow-up mattress

- Dogs allowed for an additional fee ($150/dog)
- No smoking permitted
- located in quiet cul-de-sac
- Town beach parking permits available for stays of 30 days or longer

View • Other • Barbecue/Outdoor Cooking • Laundry • Child Friendly • Wellness Facilities • Kitchen • Security/Safety • Air Conditioner • Spa • Tv • Ocean View

Private Waterfront Home: Dock, Kayaks offers accommodations in Southold, 22 miles from Splish Splash. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Private Waterfront Home: Dock, Kayaks 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 available in the vacation home. The accommodation has a fireplace. Long Island MacArthur Airport is 43 miles from the property.

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

Calendar NOT always up to date check for availability

Beach Parking good at all Southold Town Beaches Pass INCLUDED free with rental

Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees.

On the sought after 'Bayside' of the North Fork In the heart of the North Fork Wine Country and beautiful beaches we have a 1840's home with a furnished attached cottage available for weekend's, week or month rental. Apartment has small eat in kitchen, bath, living room and 2 bedrooms. One bedroom has a queen size bed the other a full size bed. Separate entrance with own lawn / patio area with lawn chairs. Comfortably furnished with Sat TV (Including HBO). Both bedrooms have center AC units. Beautiful property with century old lilacs and gorgeous perennial gardens.

- "The cottage was very comfortable and cozy. Mark and Mona are great hosts." - "The property was just perfect for us and my dog. The location is very central." - "This property was perfect for our family of 5. Our daughters (6 & 4) shared the full bed, and our baby slept in the queen room with us, in a Pack & Play. The outdoor area was very nice! The only thing we missed having was a dryer…it was humid/muggy, so after a day at the beach, our towels and bathing suits wouldn’t air dry just by being outside. Other than that, the unit had mostly everything we needed!"

Relax on the large wrap-around front porch of this Long Island, New York bed and breakfast. Free Wi-Fi and daily breakfast are offered. Cedar Beach is 1 mile away. Each uniquely styled room at A Walk in the Woods Bed and Breakfast features private bathroom. Decorated with antique accents, these rooms include a seating area. This estate is located directly on the 14 mile Bayview bicycle loop. Pindar Vineyards is 5 miles away.

- "Can’t wait to go back!" - "We will definitely be going back!" - "Excellent place to stay"

Charming cozy cottage located in the heart of the Northfork, East End of Long Island. Come explore the beautiful vineyards, farms & beaches, all within minutes from the home. Cottage is steps from the Town of Southold which offers excellent restaurants, cafes & adorable boutiques. Property sits on an acre & a half overlooking a sliver of the Peconic Bay. Located off a dirt road for the ultimate in privacy. Backyard is completely fenced in for the safety of your pup. All pups welcome! This home is impeccably maintained with high end furnishings, fully stocked chefs kitchen & luxurious linens. Bedrooms have blackout shutters for sleeping in late. Backyard has a Weber grill, hammock & outdoor furniture. And the evening star gazing is incredible. The enclosed front porch overlooks a sliver of the Bay, offering super comfy furniture for those lazy days, sipping coffee, reading your book. Cottage has a funky, cozy vibe, super relaxing. Start making your memories at this gem of a property! Welcome :)

- "We loved the property. The host was very responsive, the home was lovely, quiet, well appointed, well stocked with start up items including some goodies. I only wish I could see some water from the house although water was a short walk away. We will return." - "My family has been coming to the north fork for years. This is the first property I’ve stayed at that had a fully fenced in yard for my dog. Not only is the house perfect and fully stocked with everything (and more) that you could possibly need and want, but the yard is HUGE and beautiful. My dog was in heaven. The home is also just a short walk to downtown Southold. I highly recommend Erin’s home and I hope to return in the future. She was such a gracious host and even left us snacks and beverages. We could not have asked for a better stay."

Happiness Comes in Waves is situated in Southold, 1.6 km from Cedar Beach County Park and 37 km from Splish Splash, in an area where cycling can be enjoyed. It has a garden, a terrace, sea views and free WiFi throughout the property. The air-conditioned holiday home consists of 4 bedrooms, a living room, a fully equipped kitchen with a fridge and a coffee machine, and 3 bathrooms with a shower and free toiletries. Towels and bed linen are available in the holiday home. The nearest airport is Long Island MacArthur Airport, 72 km from the holiday home.

Kitchen • Internet • Air Conditioner • Balcony/Terrace • Parking • Child Friendly • Pet Friendly

Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and lovely screened in front porch to enjoy the beautiful pond view-watch ospreys fly over, or enjoy the pond by using kayaks, paddle boats or canoe that comes with the rental. 10 minute walk to beautiful sound beach around the corner-minutes to wineries, Southold village, and Greenport.

- "Lovely cottage with access to a beautiful large pond and use of kayak, paddleboard, acanoe. Host very responsive." - "We booked this beautiful cottage last minute for a quick weekend getaway and it was everything we hoped it would be. Eileen was also a pleasure to work with!" - "It was clean, comfortable, and had everything we needed. The gas fireplace was welcoming on a cool November evening. Location was great, 20 minutes to many of the wineries, restaurants and the beach. Canoe and kayaks were great on the small pond. It was delightful."

NF Wine Country Retreat with Dock offers accommodations in Southold, 12 miles from Long Island Railroad. The air-conditioned accommodation is 21 miles from Splish Splash, and guests can benefit from on-site private parking and complimentary Wifi. Guests can use a garden. The vacation home is composed of 1 bedroom, a fully equipped kitchen, and 2 bathrooms. A flat-screen TV is provided. The accommodation is non-smoking. Long Island MacArthur Airport is 43 miles away.

Internet • Guest Services • Barbecue/Outdoor Cooking • Ocean View • Security/Safety • Parking • View • Pet Friendly • Air Conditioner • Child Friendly • Oceanfront

Calendar NOT always up to date check for availability

Beach Parking good at all Southold Town Beaches Pass INCLUDED free with rental

Come listen to the bands while tasting the local wines (See local vineyards and events) ,

Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees.

On the sought after 'Bayside' of town In the heart of the North Fork Wine Country and beautiful beaches. We have a 1840's home with a furnished attached cottage available for weekend's, week or month rental.

Cottage has small eat in kitchen, bath, living room and 2 bedrooms. One bedroom has a queen size bed and the other a full size bed. Separate entrance with own patio area and comfortable patio furniture.

Comfortably furnished with Sat TV (Including HBO). Both bedrooms have center AC units.

Beautiful property with century old lilacs and gorgeous perennial gardens.

Ocean Beaches: The infamous 'Hampton' ocean beaches are within a 45 minute Drive.

Bay and Sound Beaches are within a few minutes from the cottage.

Vineyards: The North Fork of Long Island is famous for it's award-winning wines. Adventure out and taste them at the numerous vineyards on the North Fork.

- "The cottages at the White Blossom House are absolutely lovely. Everything about the cottage, the grounds and location were perfect. Very charming in every respect and really nice decor. Will definitely return and recommend to friends. The hosts were so wonderful and helpful. Bikes, beach passes and beach chairs were readily available super easy to access and use. Made everything that much easier and enjoyable. We had a couple of friends who live in the area we were visiting and they stopped by and we’re equally impressed with how lovely the cottages are. Perfect visit - can’t say enough good things about this lovely place."

Watersedge Retreat is located in Southold, just 1.7 miles from Cedar Beach County Park and 23 miles from Splish Splash. This vacation home is 13 miles from Long Island Railroad. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with free toiletries. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. The vacation home has a picnic area where you can spend the day outdoors. Long Island MacArthur Airport is 44 miles away.

Barbecue/Outdoor Cooking • Laundry • Ocean View • Child Friendly • Oceanfront • View • Private Beach • Security/Safety • Sports/Activities • Balcony/Terrace • Guest Services

Two bedroom PERFECT beach house located on a private beach. If you love the beach, fishing, swimming and sunsets in a quiet place, this is for YOU.
This is NOT a bluff beach. Walk right out the FRONT sliding door and you are ON the beach. Walk out the SIDE sliding door you are on the wrap around deck, with patio set barbecue grill, lounge chairs, and views in every direction. You can walk in either direction ON the beach for miles. Crystal sand, rocks, beach glass and glistening water around you. Public beaches require town parking permits which can quickly increase the cost of your stay at other non-beach front properties, but you don't need a permit since this is a private beach (no crowds, no restrictions).
57035

One Bedroom has a full size bed, the other bedroom has twin bunk beds. Wrap around deck, with furniture on BOTH sides of house for morning and afternoon sun + beach chairs included. This house does have heat for cooler nights in Spring & Fall. Perfect for a long relaxing Summer, weekend get away, or family retreat. Really great fall fishing weekends, winery trips, pumpkin picking. Give us a call, you're going to LOVE IT !

All rates listed are for a family of 4 (2 adult, 2 children). There are additional charges for extra guests and these need to be confirmed and agreed upon at time of reservation. Please note that we are vigilant about the number of people renting the house. Sorry, not pets allowed due to guests with allergies.

Keywords: House

- "We enjoyed every second of the peace & quiet. Access to the beach couldn't be better. The cottage offers comfortable accommodations both inside and outdoors and the host is just wonderful" - "Third year vacationing at this beautiful cottage overlooking the Long Island Sound! We keep coming back! Sunsets are spectacular!" - "This was our fourth stay at this lovely little house on the Long Island Sound. It is quiet and peaceful and the proximity to the beach is ideal. The sunsets are breathtaking. Gaelle communicates well and in a timely manner. Looking forward to returning in 2023."

Offering free bike hire and free WiFi access, Historic White Blosson House is a uniquely furnished inn located in Southold. The property features scenic gardens. Patio access is included with the self-catering apartment. The kitchenette is equipped with an oven and a dishwasher. The bathroom has free toiletries. An array of activities can be enjoyed on site or in the surroundings, including golfing and cycling. Southold Historic White Blossom House offers free parking. Cedar Beach Point is 7 minutes’ drive from the property. Lenz Winery is 2.3 mi away.

- "Good stay overall but with some issues"

Great location close to all the North Fork has to offer. The entire upstairs of an Historic Home built in the 1830's with quaint lower ceilings typical of 1800's with claw ft tub and full kitchen, 2 bedrooms and outside patio area with gas grill and private lawn area. Bike and Beach chair rentals available at no cost.

* Kindly note property calendar not always up to date due to multiple booking sites...please check for availability.

Vehicle Beach Parking Pass Available free with rental

- "My husband and I stayed in Apt 2 for 5 nights. The house is close to Southold beaches and all North Fork wineries and restaurants. It has a private entrance leading you upstairs to a clean 2 bedroom, 1 bath apartment. It's well maintained but very old, so be aware that it has low ceilings and even lower doorframes. My husband is 5'11" and had to duck through doorways. One of the best parts of renting this home was the host provided a parking pass and beach pass so that we could easily enjoy all Southold beaches, which were wonderful! We also enjoyed the observatory down the road; whether permitting, on Saturday nights, they open the roof for incredible views of the night sky through one of their several telescopes."

Located in Southold and within 22 miles of Splish Splash, Southold Beach Motel has a garden, non-smoking rooms, and free WiFi throughout the property. Featuring family rooms, this property also provides guests with a sun terrace. Long Island MacArthur Airport is 44 miles from the property.

- "A clean, simple motel, across from the beach with a very reasonable price!" - "I had such a relaxing weekend. Colin the owner was very attentive and always greeted everyone with a smile and a good mo" - "Great spot!" - "Had a great time attending Hampton Classic Horseshow." - "Perfect weekend stay" - "Nice place to base your North Folk Li vacation" - "Affordable gem on the North Fork" - "Excellent service, convenient, Collin very helpful."

This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Barbecue and dine in the spacious backyard with a sunset view of the lake. Stargaze with no interfering city street lights. House has two bedrooms accommodating up to four people, a large ranch-style kitchen with dishwasher, microwave and coffee maker, wifi internet access, A/C, and a TV, and DVD player. Pets allowed with prior approval. *TWO WEEK MINIMUM*

This beautifully landscaped property is one half acre in size with wooded and open areas and a private bulkheaded lakefront. It is ideal for families with young children who like to explore. The house comes completely furnished, with the exception of towels and linens.

Just down the road at the end of the lake is Peconic Dunes Camp, a summer camp operated by Suffolk County. The village of Southold is just a five minute drive away, as well as 20 of the North Fork's finest wineries. Other local visitor attractions include the historic port villiage of Greenport, Horton's Point Lighthouse, and Goldsmith's Inlet County Park.

- "A little house that had all the comforts we needed. Wonderful location and beautiful property. The house was on a pond which created beautiful waterfront views. The owner was very attentive and helpful." - "House and yard were as described. The location was close to everything yet had plenty of room for our dogs to play. Kitchen was equipped to be able to cook what we needed. Great stay in Northfork!!" - "Nice home and bigger than the home pictured. Very clean and comfortable. Great property location! Enjoyed watching the variety of birds everywhere. Would definitely recommend. Only issue sketchy internet connection."

Located in Southold, within 49 km of Montauk Point Lighthouse, Private Waterfront home Dock Kayak walk to Southold, near Greenp offers accommodation with air conditioning. It is set 35 km from Splish Splash and offers a 24-hour front desk. The holiday home is fitted with 3 bedrooms, 2 bathrooms, bed linen, towels, a TV with satellite channels, a dining area, a fully equipped kitchen, and a balcony with sea views. If you would like to discover the area, skiing is possible in the surroundings. The nearest airport is Long Island MacArthur Airport, 70 km from the holiday home.

Parking • Child Friendly

This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the deck with a sunset view of the lake and then stargaze with no interfering city street lights. *TWO WEEK MINIMUM*

Cottage has two bedrooms accommodating up to four people, air conditioning and ceiling fans, an all-electric kitchen with microwave and coffee maker, internet access and a TV and DVD player. Pets allowed with prior approval and signed pet agreement.

The property is on a beautiful one half lot with wooded and open areas and a private bulkheaded lakefront. It is ideal for families with young children who like to explore. The house comes completely furnished, with the exception of towels and linens.

Just down the road at the end of the lake is Peconic Dunes Camp, a summer camp operated by Suffolk County. The village of Southold is just a five minute drive away, as well as 30 of the North Fork's finest wineries. Other local visitor attractions include the historic port village of Greenport, Horton's Point Lighthouse, and Goldsmith's Inlet County Park.

- "My husband and I rented this cottage for most of the summer and couldn't be happier with it. We lovingly refer to this place as The Pond Shack. The house is small and rustic so if you want a luxurious rental, this isn't for you. But if you want a low key retreat at an unbeatable price in an absolutely gorgeous location with beautiful views of the Great Pond (it's really more of a lake) and a 5 minute walk to the beach, then look no further. This place is perfect for 2 couples or a couple with kids. The pond is clean and not scummy - great for swimming or just watching the water. The best thing about this place is that you feel totally in nature. We've seen a ton of Osprey, swallows, a cardinal and of course geese and there's even a swan that lives on the pond too. There are also turtles in the pond, and deer and rabbits all around the neighborhood. There are great walking/running trails just up the street and of course gorgeous Kenney's Beach with uninterrupted sound-front stretches of sand (and rocks too - bring aqua socks if you have them!). We like to walk over and watch the sunset and the water is calm and great for swimming. The owner Larry is great and we've enjoyed meeting him and interacting with him throughout our stay. He's always been very friendly, responsive and helpful. We love the North Fork and couldn't be happier to have found this gem. So sad the summer's almost over but we will definitely be back!"

Steve's Place: Heated Pool, 3BR Southold Home, Beach offers accommodations in Southold, 22 miles from Splish Splash. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Outdoor seating is also available at Steve's Place: Heated Pool, 3BR Southold Home, Beach. The accommodation 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. Guests can enjoy the outdoor swimming pool and garden at Steve's Place: Heated Pool, 3BR Southold Home, Beach. Long Island MacArthur Airport is 43 miles from the property.

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

Stay comfortably in Southold at this 2-bedroom home. This gorgeous property features 1 queen bed and one full over queen bunk bed, ensuring a terrific night's sleep for all guests. With amenities like AC, WiFi, and a washing machine, your stay will be nothing short of phenomenal. Bring your bikes for a 1-mile ride to South Harbor Beach, or enjoy local wine and food at Sophie's Bar or Croteaux Vinyards, both less than a mile from your doorstep.

- "Highly recommend Joseph and Tara's place for a wonderful getaway in Southhold. The house was immaculate and well organized, with everything you need for a relaxing stay. Joseph was very responsive and the guidelines for staying there were clear and reasonable. We highly recommend Croteaux vineyard which is a short drive away. We are excited to stay again! " - "This home was very clean and orderly. The air conditioning was FANTASTIC! It had most of what we needed. The queen bed was soft but squeaky- it was noisy every time I rolled over which made the stay a little less restful. The bottom of the bunk bed was described as “thin memory foam” by the person sleeping there, though they enjoyed sleeping on the couch. We ran the dish washer everyday because there were a limited amount of dishes. I wish there had been soap or shampoo or anything in the shower. I couldn’t find scissors anywhere! If you want to stay in a families beloved beach house- this isn’t it. It is a totally adequate and very cleanly place that feels like no one lives there. That’s not a bad thing, but you should know what you’re booking. "

This charming cedar shingled beach cottage is located steps away from Long Island Sound with stairs leading down to its own private beach. The cottage is surrounded by a wood deck perfect for watching spectacular sunsets...each night, a unique palette of pink, blue and violet sky ... as the sun drops into the water before your eyes.

The cottage has a fully equipped eat-in kitchen with dishwasher and microwave.
The modern bath has a walk-in shower.
The living room, with ceiling fan, has windows overlooking the Long Island Sound and a sliding glass door that opens onto the deck. There is an HD television with cable reception and Wi-Fi.

A barbecue, deck chairs and table with umbrella are available to enhance outdoor living.

The master bedroom has a queen bed and set of bunk beds; the second bedroom has a double bed with bunk above and another set of bunkbeds. Both have ample dresser and closet space.

A washer and dryer are conveniently located on the premises.

The surrounding area is a beach community with quaint cottages and lightly traveled roads perfect for bicycling and walking. There is excellent fishing in a nearby fresh water pond - or you can surf cast right off the deck!

Two week minimum

- "We had a wonderful few days at the cottage. The kitchen was well-equipped and loved the patio. Loved to listen to the waves! Great location near wineries, restaurants, and farm stands! Very quiet neighborhood when we were there. Enjoyed evening and morning walks on the beach and beautiful sunsets." - "The cottage was just perfect. It had everything we needed, was tidy and right there on the beach. Joan was great and we'll definitely be returning. There is only one queen bed and 6 twin bunks, so it's great for a family with kids and not ideal for a bunch of adults, but it still worked out well. Thank you Joan!"

Nestled in Southold, this delightful studio offers a superb stay for guests. Attached to our main house, this private studio apartment has a cozy bedroom nook and a charming living room featuring a comfy futon, kitchenette, and full bathroom. Overlooking your own patio with furniture, the studio is perfect for a relaxing getaway. Enjoy the convenience of WiFi, heating, AC, and more during your stay. We look forward to hosting you at our place.

- "Great location, great property. Southold is a magical place."

Experience the North Fork in our bright, happy home in the heart of wine country, just steps from beautiful Kenney's Beach, a local favorite.
Two porches for relaxing and dining.
Large, inviting living room with huge stone fireplace and queen sleeper-sofa.
Eat-in kitchen.
Spacious, shaded yard with hammock.
Walking distance to two restaurants, close to Village, wineries and many restaurants.
The Town of Southold requires a 14-day minimum stay.

- "We had a lovely vacation and the house met all of our needs. It was very clean, comfortable and well equipped. The neighborhood is quiet and is only a short walk to the beach. Nadine and Bob were fantastic host who were friendly and very accommodating. I would rent this house again." - "We had a wonderful beach vacation! Nadine and Robert were amazing hosts. They had everything we needs to ensure we had an amazing trip!" - "Nothing ostentatious but clean, comfortable and right near the beach"

Unwind in Southold at this lovely house. This tranquil retreat features 2 bedrooms, including a king bed and 2 twin beds. With amenities like a washing machine, AC, heating, and WiFi, guests can relax in this welcoming space. Enjoy your time in Southold at our cozy house. Near beach, marinas, farms & vineyards

- "The cottage was perfect for my cousin and I. It was immaculately kept and beautifully decorated. It had everything we needed and perfect distance from where we were heading for the weekend. I would stay there again in a heartbeat! So clean and cute! " - "A wonderful home to stay in for a week. A beautiful location and excellent home for a family of four. A very short drive to Southold village or a 20 minute walk. Southold was very welcoming with friendly people who always went above and beyond to help us. The home was immaculate with everything we needed. A lovely touch having snacks and drinks when we arrived. Highly recommended!!"

Sweet Southold Beach Cottage
Spring/Summer/Fall/Winter

Prime location! View Peconic Bay from your driveway! One minute walk to the BEACH at Founders Landing. A classic, North Fork renovated 2 bedroom small cottage. The petite, airy cottage with a mini split AC, 3 ceiling fans and 10 windows. Open floor plan includes a kitchen with stainless steel appliances, a counter with stools that opens to the dining area. Refreshing coastal/outdoor living includes a deck with grill. Make it your easy, breezy getaway.
Design your rental package.

MONTHLY: May 3.5k, Ju 4k, Jul 7k , Au 8k, Sep 4k
MD-LD 19k
JULY/AUG-LD 15k

WINTER 2024-2025 Oct- April 3k/mnth+util

Contact me with questions and Multiple Month Rate discount. Rates are based on a monthly rental.

Relax and enjoy the beautiful sunrise on the beach. The property is setback from the road and is on a 1/4 acre. The landscaped yard has a spacious rear deck . The petite and airy cottage has an open floor plan with a mini split AC, 3 ceiling fans, and 10 windows that let the coastal air in. The kitchen with stainless appliances and a counter with stools opens to the dining area. The cozy living room with vintage rolling doors is the perfect spot to have a morning cup of coffee as the sunrises, that’s if you don’t want to sit on the small front deck outside and see hummingbirds. The main bedroom has a large closet and laundry access. The sweet beachy bathroom includes a tub/shower, and a vintage rolling door. Enjoy the coziness of the space that embraces true North Fork coastal living.

MONTHLY: May 3.5k Ju 4k, Jul 7k , Au 8k, Sep 4k
MD-LD 19k
JULY/AUG-LD 15k

WINTER 2025-26 Oct- April 3K/month.+utl

Contact me with questions and Multiple Month Rate.

Guest Access
Kitchenwares for cooking. WiFi/Wireless internet. Bring your device to stream. 2 car driveway, house, back deck, front deck. Outdoor gas grill. Beach chairs. Bring your bikes and kayaks.

Looking forward to welcoming you. I can advise you regarding any of your interests locally and I'm happy to do so. Your privacy is respected. I may be on site to maintain the property.

The Neighborhood
Beach and water view at end of the driveway! Take a dunk before dinner. Put in your kayak or boat at the ramp. Swim at Founders Landing lifeguarded beach at end of road. The Boat Yard Marina is also at the end of road. Southold has many places to eat, small local shops, wineries and a brewery. Great hiking trails as well. Birding, Fishing, Golf, Pickleball, tennis, antiques, and rustic finds. Neighborhood is great for walking and biking and friendly faces. The North Fork offers farmstands, organic seasonal and fresh foods. Many live music venues, great restaurants and attractions.

Getting around
Walk to Southold LIRR station. Walk to Hampton JITNEY Southold. Boat. Walk to town of Southold. Local transportation includes: Car services, Uber, Lyft, bike rentals or Bring your bike. Ferry to Shelter Island, Connecticut or Sag Harbor.

Other things to note:
You are asked to be mindfull of the environment. Small dog considered. Rates are based on 2 person occupancy.
Monthly discounts are available. this property is a legal rental.

Please read the listing carefully including details.

- "We spent a week in early August at this beautiful little cottage in Southold. What a gem!!! The house is beautifully decorated and was very clean. There was everything we needed. A small private beach with lifeguard is at the end of the road 2 minute walk. We are a family with two young children aged 2 and 6 and the size of the cottage and the quiet beach with a small playground were perfect for us. The owner of the property is wonderful and gave us great tips for the area. Highly recommend a stay here! We will be back. "

Cute as a button cottage with 2 bedrooms and 1.5 bath. Oversized outside patio with large teak dining table and huge conversation seating. Private road. 1000 feet to cedar beach. Outdoor shower, kayaks and paddleboard available. Perfect for entertaining. Fire pit. Central air condition. Kitchen with dishwasher. Spacious living room. Water views from all rooms. Each bedroom has a tv with YouTube tv and other streaming services. Come enjoy your summer in this quiet beach cottage!

- "This house was wonderful for our family. Our toddler loved all the toys and we all loved the short walk to the beach. The outdoor space is gorgeous, and the neighborhood is quiet. We really enjoyed our stay!" - "This house was everything we were hoping for very short walk or drive to the beach. since it was June, we often had the beach to ourselves. The house was very well stocked with kitchenware, grill, beach gear, and a delightful outside shower. High end towels and sheets with really comfy beds. 2nd bathroom tiny but functional and adorable. We even used the fire pit with wood we purchased at the store. Very quiet and peaceful location with short drive to town. Would love to stay here again."

Classic Southold Country Charmer

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Your next adventure awaits at this charming and well-equipped home for guests of all ages! This home truly lives up to its name and will charm you from the moment you step inside. You'll find yourself grilling some veggies and patties for your loved ones in no time, thanks to the gas grill available - an ample lawn makes it an excellent place for the kids to play hide and seek or tag.

The quaint sitting area offers plenty of seating with a sofa, chairs, and even a recliner! Snuggle up on your favorite chair and turn on the flatscreen TV - you can watch your favorite movies or stream the final episode of that series you've been dying to finish. The eat-in kitchen is a delight with all the appliances you could need to prepare savory meals, snacks, and anything that comes to mind. The four-people dining table off the kitchen is perfect for group meals and game nights. The living area is sunny and furnished with nothing but comfort in mind. Get comfortable on the armchair and use the free WiFi to browse your social media.

Things to Know
AC units in bedrooms
High-speed WiFi
Vacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.

Parking notes: There is free parking available for 2 vehicles.

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

- "Perfect location, close to state parks and beautiful nature. Very well equipped kitchen- high quality cookware and dishes. Cozy, warm - but need to clean the kitchen carpet"

Minnehaha Marvel

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

This prime property with water views and surrounded by lush greenery can be your perfect place to escape reality with your loved ones. Vacation here on gorgeous Long Island, where many festivals, events, markets, shops, and local eateries abound. Take the kayaks out for a spin on the creeks and rivers, or head to the beach to participate in fun rentals and excursions like paddleboarding, surfing, boating, parasailing, and every other waterfront activity imaginable.

Upon entry, you'll be met with a bright interior and a warm feeling of welcome throughout the space. Make yourself at home by sitting on the plush furniture, curling up by the fireplace with a good book, or carrying on a conversation with loved ones. Stream a movie marathon on the large TV in the living area while the chef of the group cooks up a storm in the kitchen, equipped with stainless steel appliances, a breakfast bar, and a formal dining table. The main suite is comfortable, with plenty of room to get a great night's rest from the day's activities. It boasts a TV for private viewing, a spacious closet, and a lovely en suite bathroom with a walk-in shower. Enjoy grilling barbecue and dining alfresco on the back patio, witnessing spectacular sunsets along the bay.

THINGS TO KNOW
Vacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.
Parking notes: No parking available.

Please note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

- "Nice stay"

BEAUTIFUL North Fork Just renovated cottage in Founders Landing Beach Community in Historic Southold Village - - very short walk to wonderful Bay beach with lifeguard, Walk from jitney and LIRR Southold stop. Delightful setting with exquisite mature gardens, walk to nearby restaurants; North Fork Table, Grateful Deli, Michelangelo's, Southold Social, North Fork Roasters, Juice Bar and Yoga studio, local farm stands, Marina, oyster farm, IGA grocery store, Historic Southold Village Museum.
Very short drive or bike ride to many vineyards and Long Island Sound beaches, Shelter Island Ferry and a quick 3 mile drive or bike ride to the Maritime Village of Greenport with seaport, many restaurants, and shops. Official Southold rental permit in hand.

This lovely 2 bedroom cottage is furnished with antiques and new comfortable Pottery Barn beds. Air-conditioners, ceiling fans and central heat. New renovated kitchen and bathroom, enclosed porch, and outdoor dining table and chairs, outdoor shower, BBQ Grill. Home has Adirondack chars and fire pit. Hot tub, Kayak, beach chairs and beach cart, kayak, fishing rods and bicycles. Complete with everything needed for a wonderful vacation and romantic beach getaway. Ideal for a couple or young family that loves outdoors: Wonderful bay beach w/ lifeguard just a few blocks down the street.
Available NOW thru end of May ( possibly longer ) - two week minimum. Usually rentals are Saturday to Saturday but there's some flexibility on check-in/out day of the week. We prefer to rent for for one month minimum, but flexible. Summer rates TBD.
If interested, make arrangements to visit !

- "It is with great pleasure we are the first reviewer of this lovely traditional cottage. The facilities are tremendous , wifi , BBQ, plenty of space , pretty garden and marvelous location. As serial holiday renters over the years , we hit gold with this cottage. Steve allowed us use of the bikes, kayak and hot tub. Cottage is c 500 m from a quiet safe Bach which had plenty of space despite peak timings. The village centre is a short walk away with all the facilities you need. comfortable, relaxing and easy living - well done Steve we wish you every success Mark and Anne UK ."

Completely renovated 60's ranch, 2 bedrooms with queen sleeper sofa in family room to sleep 6, new appliances, washer/dryer, large front shaded deck overlooks natural landscape lot, cathedral ceiling in living/dining area; 2 sliding glass doors to front and back patios; outdoor shower; wood-burning fireplace; gas grill, parking for 3 cars......................................................................................................................

- "We wanted to escape the city for a few weeks and absolutely loved staying at Steve’s property! The description of the house was accurate- it was renovated, clean, everything was nearby and convenient. Steve was very responsive and tried to make our stay as pleasurable as possible. We would definitely come back!"

CHECK OUT OUR REDUCED SEASONAL RATES
6 WINERIES IN UNDER A MILE
NO CLEANING FEES
NO EXTRA PERSON FEES
FREE BIKES
FREE BEACH PASSES

This listing is for one room in a Bed and Breakfast. We're a genuine, licensed B&B. Experience this Insta-ready, newly renovated 1820 farmhouse. Your comfort and relaxation are our goal; designer flourishes are inside and out, filled with unique all-new furnishings. Our Salon features the latest in the arts: sculpture, painting, poetry, readings. Nothing has been overlooked.

- "Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great vibes here. A memorable experience I hope to have an opportunity to repeat soon."

Beautifully appointed and ultra-comfortable home with sunny, sky-lit, open floor plan. 2+ Bed/2 Bath Southold getaway with extra-large bilevel deck. A short walk/bike ride or about a minute’s drive to Kenney's Beach, the sandiest sound beach on the North Fork with the most spectacular sunsets. Heart of wine country, close to town and all amenities. Master suite with washer/dryer, 2nd bedroom sleeps up to 3, plus den with futon couch. Central AC, ceiling fans, gas grill. House has a piano, turntable, bluetooth speaker setup, fast wifi, well-stocked kitchen and other conveniences. Each party will receive a welcome pack of local goodies. Pets allowed on a case-by-case basis.

- "Bright and cheery beach cottage with a spacious kitchen and huge brand new outdoor space perfect for lounging/grilling and surrounded by trees (felt very sheltered from street and neighbors). Half the nights of our stay we cooked at the house and enjoyed dinner on the beautiful deck! We brought our bikes and loved the super quick ride to the beach, but also walked a few times which was just under ten minutes. The owners were extremely communicative and very sweet as they left us a LOVELY north fork welcome basket. The house was also very well equipped for any kind of cooking or baking you desire. Thank you so much, Glen, for a wonderful stay!"

Enjoy a stylish experience at this centrally-located historic charmer. Have cocktails on the balcony, cook in the fully modern chef’s kitchen, grill and dine on the patio and enjoy the sauna. Walk to the beach and stop a local winery on the way home.
Close to Greenport and Southold.

Child Friendly • Security/Safety

Experience the perfect blend of tranquility and convenience at our zen farmhouse. Nestled close to stunning beaches and renowned vineyards, this serene retreat features a spacious, light-filled interior with natural materials and minimalist design. The gourmet kitchen and an open floor plan

The backyard is a private sanctuary: a saltwater pool surrounded by lush evergreen gardens. Enjoy outdoor living with a patio and shaded lounge areas. Plus, Southold town is just a short walk away, offering easy access to local shops and dining. This property provides a peaceful escape with everything you need nearby.

****2 week minimum ****
Permit #0361
NO DOGS
Guest access
2,500 square feet property + saltwater pool

Internet • Air Conditioner • Accessibility • Guest Services • View • Balcony/Terrace • Kitchen • Other • Security/Safety • Laundry • Parking • Child Friendly