Vacation rentals in Southampton

4.79 out of 5 average rating, 43 reviews

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

4.9 out of 5 average rating, 99 reviews

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

5 out of 5 average rating, 101 reviews

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

4.88 out of 5 average rating, 102 reviews

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

5 out of 5 average rating, 11 reviews

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.9 out of 5 average rating, 115 reviews

An outdoor deck area is seen featuring a large round table surrounded by several comfortable chairs. A sun umbrella provides shade, while a propane grill is positioned nearby. Lush trees create a natural backdrop, enhancing the serene atmosphere of the space.

Home in Shelter Island

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Cottage in Shelter Island

A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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What guests are saying

Direct Shoreline Long Island Sound Waterfront

4.95 out of 5 average rating, 80 reviews7 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Cottage in Guilford

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in North Fork

What guests are saying

Black Point Retreat - Entertain & Enjoy the Beach!

5 out of 5 average rating, 10 reviews7 months ago

Our group had a wonderful stay at this beautiful, spacious home. It was spotlessly clean and well stocked with supplies. The 7 of us enjoyed gathering around a spacious table to play games in the bright roomy sunroom. It led out to a very nice patio with a comfy wicker couch and chairs. The host was very prompt in responding to us and was quick to satisfactorily address our questions. We had a wonderful,memorable time!

Home in East Lyme

What guests are saying

La Sirena Beach Cottage

4.96 out of 5 average rating, 24 reviews3 days ago

House was just as it looked in the pictures - beautifully decorated. Has everything needed for a vacation. Comfortable, bright and cheerful. Back yard was private. House was fully stocked with what was needed along with beach supplies in the outdoor shed. Quick walk to the beach. Would easily rent again!

Home in Woodmont

What guests are saying

The Sandy Shack - Coastal Escape

4.9 out of 5 average rating, 21 reviews6 days ago

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Home in North Fork

What guests are saying

Hop Skip and a Jump to the Beach

4.97 out of 5 average rating, 35 reviews8 months ago

Our first ever stay at 'Hop Skip and Jump' really met all of our expectations and needs for the week of 8/10-8/17/24! I have never in my 70+ years of spending a summer week in Old Lyme been so enveloped with 5 star luxury while at the Beach! I would recommend this rental to any small family or a group of girlfriends! Hop

Cottage in Old Lyme

What guests are saying

Seaside Paradise

5 out of 5 average rating, 5 reviews4 months ago

We stay 4 weeks at Jacqueline place, everything was great, did not have any problem. Place is exactly fit the advertising if not better and everything was clean and working. We find place and the area is so peaceful and quiet. Perfect location for someone just looking for rest in very beautiful neighborhood. Jacqueline was very responsive, easy to communicate, helpful and polite. I would definitely stay again and recommend for anyone needs a place feels like home away home.

Home in Milford

What guests are saying

Captains Quarters | July avail!

5 out of 5 average rating, 16 reviews1 month ago

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Home in East Hampton

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Popular amenities for Southampton vacation rentals

Stay near Southampton's top sights

Cooper's Beach, Southampton112 locals recommend

Parrish Art Museum262 locals recommend

Oakland's Restaurant & Marina104 locals recommend

Village of Southampton98 locals recommend

Duck Walk Vineyard94 locals recommend

Sant Ambroeus83 locals recommend

House rentals in Southampton

4.77 out of 5 average rating, 84 reviews

A spacious backyard is featured, showcasing a well-maintained lawn, a volleyball/badminton net, and a pool surrounded by landscaping. The home is visible in the background, framed by trees that display seasonal foliage under a clear blue sky.

Home in Hampton Bays

Hamptons Retreat | Pool, Volleyball, Jacuzzi

4.85 out of 5 average rating, 160 reviews

A charming Cape Cod cottage is showcased, featuring a light gray shingled exterior and blue door. The front yard is adorned with green grass and small shrubs, while steps lead to the entrance. Tall trees frame the property, providing a sense of privacy.

Home in Sag Harbor

Sag Harbor House for rent.

4.89 out of 5 average rating, 101 reviews

The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.

Home in East Haven

Welcome To Piper's Rest

4.96 out of 5 average rating, 119 reviews

A traditional two-story house is framed by well-maintained greenery and shrubs. A paved driveway leads to the entrance, while a detached garage is visible to the side. The exterior features white siding with red trim and multiple windows, creating a welcoming appearance.

Home in Southampton

4 Bed, 2 Bath, Southampton, L.I.

4.95 out of 5 average rating, 230 reviews

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

Private beach, fully updated cottage, on 2 acres.

4.97 out of 5 average rating, 121 reviews

The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.

Home in Old Saybrook

Year Round Beach House in Old Saybrook, CT.- Pets

4.58 out of 5 average rating, 137 reviews

A neatly landscaped exterior features a charming entryway with a brick pathway leading to the front door. Flanked by mature shrubs and seasonal flowers, the home is designed with a textured façade, windowed accents, and a stairway that invites guests indoors.

Home in Lake Ronkonkoma

Spacious 3 Bdrm Bohemia Holbrook Stony Brook

4.99 out of 5 average rating, 101 reviews

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

Home in Montauk

6 minute walk to Ditch Plains Beach

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Beach house rentals in Southampton

4.93 out of 5 average rating, 351 reviews

A sunlit view of a sandy beach stretches towards the horizon, with gentle waves lapping at the shore. Colorful umbrellas dot the sandy area, and a wooden walkway runs parallel to the beachfront. In the distance, sailboats can be seen on the calm water.

Home in New London

Amazing Beach House

4.84 out of 5 average rating, 55 reviews

A stunning view of the beach and water extends from a balcony. The calm sea reflects the sky's hues, while a sandy shore and a low wooden dock are visible. Bright sunlight illuminates the scene from a hanging light fixture above.

Home in Milford

Newly Built Beach House Getaway

The image captures a serene beach at sunset, where gentle waves lap against the shore. The sky displays a gradient of colors from warm oranges to cool purples, reflected softly on the water's surface. The distant cliffs are outlined against the colorful horizon.

4.81 out of 5 average rating, 90 reviews

Summer Retreat at the beach , enjoy Wine Country

4.92 out of 5 average rating, 25 reviews

A modern living room features a blend of cozy seating options in rich colors, including curved sofas in green and orange. A marble coffee table occupies the center, set on a light rug. Natural light floods in through large windows, illuminating the stylish decor.

Home in West Haven

Westshore Luxury

4.82 out of 5 average rating, 11 reviews

The entrance features a welcoming door with an emblem above. A wooden deck with a table and chairs is visible, offering a casual outdoor seating area. The surrounding landscape shows a gravel area and additional structures in the distance, suggesting a beach community setting.

Home in Westbrook

Beachside @ 455 Seaside

4.95 out of 5 average rating, 19 reviews

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

Beach House steps from sand & Amazing Views

4.96 out of 5 average rating, 186 reviews

The image captures a serene view of the ocean from a wooden porch, showcasing calm waters and a sandy beach. A neatly maintained lawn extends to the shoreline, with a few small boats visible in the distance under a clear blue sky.

Home in East Lyme

Beachfront Paradise

4.92 out of 5 average rating, 25 reviews

A modern living space features a mounted flat-screen TV on a white wall, complemented by a sleek black cabinet. A small white desk with a chair is positioned nearby, and natural light floods the area from a light fixture above. Stairs lead to the upper level.

Home in Milford

Modern Beach Mood 2!

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Lakefront house rentals in Southampton

The bedroom features a patterned bedspread and cozy pillows, with two windows providing natural light. Glass doors lead to a private deck overlooking the lake, framed by a simple rug and an outdoor seating area, enhancing the connection to the serene waterfront.

4.94 out of 5 average rating, 31 reviews

Waterfront NoFo Cottage w/ public beach access

4.83 out of 5 average rating, 12 reviews

A modern kitchen and dining area is showcased with light wood flooring and white shiplap walls. A round wooden table with black chairs is positioned near a large window, allowing natural light to fill the space. The kitchen features dark cabinetry and a central island.

Home in Clinton

Boulder Lake House Retreat

4.95 out of 5 average rating, 60 reviews

Large glass doors create a connection to the outdoors, allowing views of greenery and water. A hammock hangs outside, emphasizing relaxation. A spacious seating area is faintly visible, complemented by a wooden table and white chairs. Decorative hats are placed on the shelf above the doorway.

Home in Montauk

Waterfront Home with Private Beach

The entrance of a coastal cottage is framed by natural wood shingles. A light blue door stands out under a covered porch, surrounded by potted flowers in white and purple. Lanterns add gentle illumination, while a decorative pumpkin and a blue pumpkin provide seasonal accents.

4.91 out of 5 average rating, 23 reviews

Coastal Cottage on the Water

4.96 out of 5 average rating, 25 reviews

A wooden deck is positioned beside a calm lake, surrounded by leafy trees. The deck offers an unobstructed view of the water and greenery, creating a serene outdoor space for relaxation. Natural light filters through the leaves, enhancing the peaceful atmosphere.

Home in Clinton

Zaku’s Lake House

5 out of 5 average rating, 3 reviews

A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.

Home in Hampton Bays

Hamptons Waterview Cottage

4.88 out of 5 average rating, 146 reviews

A bright and airy living area features high ceilings with exposed rafters and reclaimed wood beams. A red front door adds a pop of color. Comfortable seating options are provided with a white sofa and armchairs, while a wooden coffee table and a dining table accent the space.

Home in Montauk

Waterfront House on Fort Pond, MTK