Vacation rentals in Wainscott

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Top-rated vacation rentals in Wainscott

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Guest favorite
A sparkling heated pool is framed by wooden decking, surrounded by lush greenery. Sunlight reflects off the clear blue water, creating a refreshing atmosphere. Lounge chairs are positioned nearby, offering a comfortable space for relaxation.
Home in Bridgehampton
4.76 out of 5 average rating, 51 reviews

Cheerful 3 bedrm-4 beds-3 bath -beach home w pool

Heart of the Hamptons is situated this bright, beach house 5 min from the ocean, BH/Sag Harbor town, & Wolfer vineyards. 2 master suites w/ ensuite bathrooms and an additional guest room with adjacent bathroom that comfortably sleeps 6 -1 King, 1 queen, 2 twin. Open kitchen that adjoins the dining area and the double height living room w/ fireplace. Sparkling heated (add charge) pool (MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway

Top guest favorite
A spacious bedroom is featured with a comfortable king-sized bed, adorned with soft linen and decorative pillows. Nightstands with stylish lamps provide gentle illumination, complementing the calm color scheme of the room.
Apartment in Bridgehampton
4.96 out of 5 average rating, 81 reviews

Hamptons Elegant and Comfortable Apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

Top guest favorite
Home in Springs
4.91 out of 5 average rating, 128 reviews

Serenity + privacy; 1 block to waterfront dining

Enjoy the privacy and space of your own home! Located near all of the best Hampton's attractions. Enjoy your large home surrounded by nature and serenity. Swim in your pool, spark up the BBQ + firepit, enjoy al fresco dining under the stars. Stream on your 80' TV + cook in your large Chef's kitchen. Stroll just 1 block to the best waterfront dining + cafe for drinks/dinner/morning coffee on the sea. You will be 8 mins to Main St., 10 mins to beaches, close to museums, coffee + so much more!

Guest favorite
A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.
Apartment in Sag Harbor
4.91 out of 5 average rating, 171 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Superhost
The charming exterior of a cedar shingle house is framed by lush greenery. A welcoming entryway features a blue front door, complemented by symmetrical windows on either side. The landscaped front yard includes low shrubs and a gravel pathway leading to the entrance.
Home in East Hampton
4.77 out of 5 average rating, 65 reviews

Beautiful E. Hampton Home w/ Brand New heated pool

RECENTLY RENOVATED BASEMENT LEVEL SEE PICS Charming and beautifully designed, our East Hampton home is the perfect getaway. Enjoy a HEATED pool and easy access to local attractions - we're just 2 miles from the village and a short drive to the beach. Inside, you'll find three large HD TVs with cable and internet, as well as gas grill for summer fun. Our private entry lower apartment includes a kitchenette, full bath, and many extras. Book your stay today and experience luxury and relaxation!

Guest favorite
A contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.
Home in East Hampton
4.97 out of 5 average rating, 161 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Top guest favorite
The exterior of the cottage is presented, showcasing a two-story wooden structure with dark wooden siding. Two windows are visible on the upper floor, framed by natural greenery. A small porch area, with stone accents, invites guests to step inside.
Guesthouse in East Hampton
5 out of 5 average rating, 18 reviews

Peaceful cottage

Take a break and unwind at this quiet, peaceful retreat! This 3 level cottage includes lower level garage parking for one car and laundry. The main level holds a full kitchen, spacious living room, and half bath. The second floor bedroom has an en-suite bathroom. Situated beside the main house, on 2.5 acres surrounded by forest, with easy access to trails. Close to ocean and bay beaches, midway between East Hampton and Sag Harbor. Perfect for a couple with an appreciation for nature!

Guest favorite
A spacious backyard is showcased, featuring a large saltwater pool surrounded by six lounge chairs. Lush green grass is complemented by a flowerbed, while tall trees provide shade. The house, with a wooden deck, is visible in the background.
Home in Sag Harbor
4.94 out of 5 average rating, 16 reviews

Hamptons Home w/ Salt Water Pool

3 Bed/ 2 Bath Sag Harbor Retreat w/ Salt Water Pool. Nestled close to both Sag Harbor Village and Sagaponack, this charming home offers the perfect blend of comfort and convenience. With 3 bedrooms, 2 baths, and situated on a generous .66-acre lot. Outdoors, the expansive yard features a 35x17 saltwater pool. Located just moments from Sag Harbor Village, you'll enjoy easy access to boutique shops, acclaimed restaurants, Wolffer Estate Vineyards, and picturesque waterfront views.

Top guest favorite
A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.
Guest suite in Sag Harbor
4.9 out of 5 average rating, 395 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

Top guest favorite
A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.
Apartment in Sag Harbor
4.94 out of 5 average rating, 142 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Top guest favorite
Guest suite in East Hampton
4.97 out of 5 average rating, 174 reviews

Super sweet king en-suite prvt access pool central

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Top guest favorite
The living area features two comfortable sofas, a wooden coffee table, and a dining table set for four. A window allows natural light to fill the space, while decor accents create a relaxed environment. Air conditioning unit is visible on the wall.
Cottage in East Hampton
4.98 out of 5 average rating, 371 reviews

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

Popular amenities for Wainscott vacation rentals

When is the best time to visit Wainscott?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€597€608€602€602€738€906€1,172€1,204€804€597€597€623
Avg. temp0°C1°C4°C10°C15°C21°C24°C23°C19°C13°C8°C3°C

Frequently Asked Questions

  • 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.

  • How much does it cost to stay in house rentals in Wainscott?

    Experience the best of Wainscott with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Wainscott?

    Four-legged friends are welcome in Wainscott. Choose from more than 170 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Wainscott?

    Yes! Work meets play with ease at over 210 vacation rentals in Wainscott featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Wainscott vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 310 vacation homes with pools in Wainscott, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Wainscott?

    Make yourself at home in Wainscott by choosing from our most frequently booked neighborhoods. We have over 840 vacation rentals in Sagaponack, and over 2,150 vacation rentals in Wainscott.

  • 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.

  • 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.

  • 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 free parking?

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

Quick stats about vacation rentals in Wainscott

  • Total vacation rentals

    Explore 360 vacation rentals in Wainscott

  • Nightly prices starting at

    Wainscott vacation rentals start at €77 per night before taxes and fees

  • Verified guest reviews

    Over 5,920 verified reviews to help you choose

  • Family-friendly vacation rentals

    330 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 170 rentals that welcome pets

  • Vacation rentals with a pool

    310 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    360 of Wainscott vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wainscott rentals

  • 4.9 Average rating

    Wainscott stays are highly rated by guests—averaging 4.9 out of 5!

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