Vacation rentals in Wainscott

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Top-rated vacation rentals in Wainscott

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

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Top guest favorite
A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.
Home in Springs
4.95 out of 5 average rating, 253 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Guest favorite
A two-story beach house features wooden shingle siding and large windows. A sparkling blue pool is positioned in the foreground, surrounded by a wooden deck. Comfortable lounge chairs are placed nearby, offering options for relaxation outdoors.
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

Serene, private, Hamptons oasis; 1 block to dining

Experience the calm and stillness of this serene home. Enjoy the privacy of your own space. Designed to be a zen oasis for you! Relax poolside with nature surrounding you; you may spot a deer or bunny on the property! Spark up the BBQ + firepit under the starry sky; sip your morning coffee on the porch, enjoy 80' streaming TV. You will be in an ideal location; you can walk just 1 block to waterfront cafe + dining w/ the best sunsets. Drive 3-10 minutes to Main Street, beaches + so much more!

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, 160 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
A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.
Apartment in Sag Harbor
4.99 out of 5 average rating, 220 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

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, 394 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, 139 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
A rustic wooden fence displays a sign reading 'BEACHGLASS BARN' in light blue paint. Colorful flowers peek through the fence, adding a touch of nature to the setting. The surrounding greenery enhances the inviting atmosphere of the property.
Guest suite in East Hampton
4.97 out of 5 average rating, 174 reviews

King suite w 2bths Prvt pool&entrance Close 2 all

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
A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.
Home in Sag Harbor
4.89 out of 5 average rating, 111 reviews

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

Guest favorite
An inviting in-ground pool is surrounded by lush greenery and vibrant trees. Sunlight reflects off the clear blue water, enhancing the serene atmosphere. Outdoor seating can be seen nearby, providing a tranquil spot to relax amidst the natural setting.
Guest suite in Springs
4.9 out of 5 average rating, 252 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

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, 370 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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