Are there Wainscott house rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 290 house rentals with pools in Wainscott, available on Airbnb. Make a splash and soak up the sun in style!

Are there pet-friendly vacation rentals in Wainscott?

Four-legged friends are welcome in Wainscott. Choose from more than 160 vacation rentals for guests traveling with pets.

Do house rentals in Wainscott have air conditioning?

Absolutely! We offer over 330 house rentals with air conditioning in Wainscott. Enjoy a tailored experience with all the comforts you desire.

Are there vacation rentals with a dedicated workspace in Wainscott?

Yes! Work meets play with ease at over 220 vacation rentals in Wainscott featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do house rentals in Wainscott have wifi?

Absolutely! We offer over 330 house rentals with wifi in Wainscott. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Wainscott have a kitchen?

Absolutely! We offer over 310 house rentals with a kitchen in Wainscott. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Wainscott?

Enhance your stay in our House Rentals with the most popular amenities: over 330 homes with wifi, over 320 homes with free parking, over 310 homes with a kitchen, over 330 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

How much does it cost to stay in apartment rentals in Wainscott?

Experience the best of Wainscott with our apartment rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Are there family-friendly vacation rentals in Wainscott?

Wainscott has more than 330 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Do house rentals in Wainscott have free parking?

Absolutely! We offer over 320 house rentals with free parking in Wainscott. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Wainscott

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Wainscott

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A spacious living room is defined by a sectional sofa, complemented by a wooden coffee table at the center. Natural light filters through large windows adorned with sheer curtains. Light-colored walls and decorative wall art enhance the inviting ambiance.

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom and a second bathroom as part of an open primary suite. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Sorry but, absolutely no animals as owner has severe allergy.

Guest favorite

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.

Home in North Fork

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.

Guest favorite

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

4.88 out of 5 average rating, 102 reviews

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

Guest favorite

A small outdoor seating area features a round table with a woven tray holding glasses, complemented by two comfortable chairs. The view extends over the calm waters of the Peconic River, with boats moored nearby and trees lining the shore under a clear blue sky.

Houseboat in North Fork

5 out of 5 average rating, 11 reviews

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!

Superhost

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. Beach grass and wooden fencing line the path leading to the water, where a lifeguard stand is positioned for safety.

Home in Hampton Bays

4.8 out of 5 average rating, 69 reviews

Spacious Hamptons Oasis | Perfect for Families

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

Guest favorite

A light-filled living room features vaulted ceilings with wooden beams. A comfortable seating arrangement includes two white sofas and a wicker chair, with a wooden coffee table at the center. A wall-mounted television and a fireplace are positioned for relaxation, with large windows offering views of the outdoors.

Home in Montauk

5 out of 5 average rating, 6 reviews

Hilltop Bright Home w/New Pool Summer 2024

Home is professionally managed by Montauk Rental Management Group. Your family will be close to everything when you stay at this centrally-located Montauk home. Short drive to Town and Beaches. This home was recently painted and updated, it's clean, bright and the perfect family rental! -4 bedrooms -3 bathrooms -Spacious deck with water views -Outdoor dining & seating -Grill -Peaceful, quiet location perched on a hill Rental Registry 23-780

Superhost

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

4.9 out of 5 average rating, 115 reviews

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$.

Top guest favorite

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.

Home in North Fork

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.

Guest favorite

The exterior of the beach house showcases a rustic wooden facade complemented by extensive outdoor decking. A hot tub is visible on the lower level, surrounded by a landscaped yard filled with lush greenery. A balcony extends from the upper level, enhancing the outdoor living space.

Home in Montauk

4.92 out of 5 average rating, 51 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy. We are also pet friendly!

Top guest favorite

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.

Cottage in Shelter Island

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...

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Wainscott vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Wainscott's top sights

Wölffer Estate Vineyard277 locals recommend

American Hotel124 locals recommend

Sen81 locals recommend

Sag Harbor Whaling and Historical Museum77 locals recommend

Lulu Kitchen & Bar62 locals recommend

Sag Pizza59 locals recommend

Other great vacation rentals in Wainscott

Superhost

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

Guest favorite

A spacious great room is highlighted by a cathedral ceiling with exposed wooden beams. Comfortable sofas frame a central coffee table, while large windows provide natural light, accentuated by sheer white curtains. A cozy reading nook is positioned against the wall, complemented by a variety of books.

Cottage in North Fork

5 out of 5 average rating, 13 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Guest favorite

A well-maintained pool area is set against a backdrop of lush greenery, featuring a shimmering pool surrounded by lounge chairs. Sun umbrellas provide shaded spots, and a trampoline is visible in the distance, adding to the outdoor recreational space.

Home in Hampton Bays

5 out of 5 average rating, 9 reviews

Hampton Bays Hideaway!

Guest favorite

A waterfront balcony is featured, showcasing wood paneling and a clear view of the water. The deck is equipped with a railing and lights, offering a relaxing spot to enjoy the scenery. The sunlight casts shadows along the planks, highlighting the serene environment.

Home in North Fork

5 out of 5 average rating, 10 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Top guest favorite

An outdoor space features a clear blue swimming pool surrounded by a stylish patio. Lounge chairs and umbrellas provide shaded seating areas, while lush green landscaping and decorative gravel enhance the serene environment.

Home in East Patchogue

5 out of 5 average rating, 20 reviews

Ho Hum Holiday In Bellport with Pool

Guest favorite

A bright living room features a high wooden ceiling and large windows, allowing natural light to fill the space. Comfortable seating options include a spacious sofa and woven chairs. A decorative area rug is positioned on wood flooring, creating a cozy gathering place.

Home in Hampton Bays

4.89 out of 5 average rating, 99 reviews

Hamptons Escape minutes from Beaches and Nightlife

Guest favorite

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

4.89 out of 5 average rating, 485 reviews

Great little place just for a couple

Guest favorite

A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.

Guesthouse in Shelter Island

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

Show all

Quick stats about vacation rentals in Wainscott

Total rentals
370 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
5.4K reviews
Family-friendly rentals
330 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
310 properties have a pool

Frequently Asked Questions

Are there Wainscott house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 290 house rentals with pools in Wainscott, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Wainscott?
Four-legged friends are welcome in Wainscott. Choose from more than 160 vacation rentals for guests traveling with pets.
Do house rentals in Wainscott have air conditioning?
Absolutely! We offer over 330 house rentals with air conditioning in Wainscott. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Wainscott?
Yes! Work meets play with ease at over 220 vacation rentals in Wainscott featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Wainscott have wifi?
Absolutely! We offer over 330 house rentals with wifi in Wainscott. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wainscott have a kitchen?
Absolutely! We offer over 310 house rentals with a kitchen in Wainscott. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Wainscott?
Enhance your stay in our House Rentals with the most popular amenities: over 330 homes with wifi, over 320 homes with free parking, over 310 homes with a kitchen, over 330 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in apartment rentals in Wainscott?
Experience the best of Wainscott with our apartment rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Wainscott?
Wainscott has more than 330 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Wainscott have free parking?
Absolutely! We offer over 320 house rentals with free parking in Wainscott. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Wainscott

Top-rated vacation rentals in Wainscott

Vacation rentals for every style

Popular amenities for Wainscott vacation rentals

Stay near Wainscott's top sights

Other great vacation rentals in Wainscott

Quick stats about vacation rentals in Wainscott

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Frequently Asked Questions

Destinations to explore