Vacation rentals in Wainscott

4.92 out of 5 average rating, 26 reviews

A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Woodmont

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

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!

4.82 out of 5 average rating, 68 reviews

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

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!

Guesthouse in Westhampton Beach

A charming guesthouse is illuminated by a warm light above the door, showcasing its well-maintained exterior. The inviting entrance features a single door and multiple small windows, framed by greenery and a pathway leading to the entrance.

5 out of 5 average rating, 3 reviews

Summer retreat cottage in WHB

Lovely guesthouse with private patio. Steps to Main Street and houses of worship. Enjoy walking or biking to the farmer's market, restaurants, marina, and beach. Bright kitchen and comfortable living room with wifi and smart tv. BBQ and outdoor shower for your use (located on the patio of the main house). Beach pass available for stays of 30+days; access to private village beaches before 10am and after 5pm as per village policy.

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$.

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.

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.

4.92 out of 5 average rating, 51 reviews

A spacious outdoor deck features a hot tub and comfortable seating area, surrounded by lush greenery. The inviting hot tub offers a relaxing retreat, while the seating includes a large sofa and a coffee table, creating an ideal space for outdoor gatherings.

Home in Montauk

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

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A space thats all yours, with room for everyone

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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

A serene beach landscape stretches along the coastline, with soft, sandy shores meeting calm waters under a clear blue sky. Gentle waves lap at the shoreline, and greenery borders the edge of the beach, creating a tranquil atmosphere.

4.81 out of 5 average rating, 90 reviews

Summer Retreat at the beach , enjoy Wine Country

4.87 out of 5 average rating, 153 reviews

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

A-Frame cabin with private beach & epic sunsets

5 out of 5 average rating, 13 reviews

Cottage in North Fork

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

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.

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

4.89 out of 5 average rating, 99 reviews

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

Hamptons Escape minutes from Beaches and Nightlife

4.89 out of 5 average rating, 484 reviews

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

Great little place just for a couple