Holiday rentals in Wainscott

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Top-rated holiday rentals in Wainscott

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Guest favourite
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, 156 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 favourite
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, 388 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. Ideal for a fall or winter visit to explore the area during the quieter season. 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. Fully self contained and private.

Superhost
A cozy bedroom is shown, featuring a spacious bed adorned with a floral quilt. Light streams through multiple windows, illuminating the room. A white dresser and closet are visible, while a green yard can be seen through the windows.
Home in East Hampton
4.82 out of 5 average rating, 138 reviews

Sunny & Serene Private Cottage near Downtown EH

Our lovely one-bedroom cottage sits on a quiet lane 3/4 of a mile from downtown East Hampton. The cottage is light and bright, with whitewashed walls, vaulted ceilings and skylights, lots of windows and beautiful minimalist décor. It's an incredibly peaceful place to wake up in the morning, with a gorgeous green yard right outside the many bedroom windows. Every bay and ocean beach around East Hampton is 5-10 minutes away and Nick and Toni's is less than a 10 minute walk.

Top guest favourite
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.
Flat in Sag Harbor
4.93 out of 5 average rating, 136 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 .

Guest favourite
A charming house is presented, featuring a blend of shingled and brick exterior. The porch is outlined by neatly trimmed hedges, and a gravel pathway leads to the entrance. Lush greenery surrounds the home, accentuating its inviting curb appeal.
Home in East Hampton
4.94 out of 5 average rating, 34 reviews

East hampton 3 bedroom home w/ pool great location

Welcome to your hamptons summer home! Amazing location 5 minutes from both Sag Harbor and East Hampton towns and 10 minutes to Bridge Hampton. Beautifully landscaped backyard with heated pool and bbq. The primary bedroom includes a king bed, the 2 secondary bedrooms have queen beds. Open floor plan with kitchen and dining room flowing to the backyard is perfect for indoor/outdoor lunch and dinners. 2 full bathrooms and central air.

Top guest favourite
A bright living area features large windows providing views of the bay. Seating includes a white sofa and wooden chairs, while a natural wood coffee table anchors the space. A dining table for six is visible in the background, complemented by stylish light fixtures.
Bungalow in Springs
5 out of 5 average rating, 19 reviews

Charming Bungalow on the Bay

This newly remodeled 1960’s bungalow is the perfect getaway for couples and families alike. Located right on Gardiner’s Bay, there’s a gorgeous view of the water from the large windows and front porch. From the front steps you can follow the 300 yard path to your own private beach where you can wade, swim, snorkel, paddleboard, or just enjoy the amazing view and salt air. (East Hampton Rental Registry Certificate Number: 24-234)

Guest favourite
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

Guest favourite
An expansive view of the ocean stretches across the horizon, framed by wooden sliding doors. Gentle waves wash onto a sandy beach, with greenery in the foreground. A potted plant rests on the railing, adding a natural touch to the serene scene.
Flat in Montauk
4.88 out of 5 average rating, 128 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Guest favourite
The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.
Guest suite in North Fork
4.88 out of 5 average rating, 715 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Top guest favourite
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
4.97 out of 5 average rating, 358 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).

Top guest favourite
A bright living area is depicted, featuring a sleek sofa, a wooden coffee table, and a round dining table surrounded by red chairs. The space incorporates a large potted plant, and light streams through a nearby window, illuminating the whitewashed wood floors.
Flat in East Hampton
4.97 out of 5 average rating, 129 reviews

Renovated Guest Cottage close to E.Hampton Village

This modern beach guesthouse has white washed wood floors, all new stainless steel appliances , central air, and very conveniently located . We are a short walk to East Hampton Village and 1.9 miles to the nearest beach.There is a private back patio with a cedar outdoor shower and sitting area in a serene setting .

Guest favourite
A comfortable living area features two light-colored sofas with decorative pillows, arranged around a central glass coffee table. A flat-screen TV is mounted on the wall, and large sliding doors provide scenic views of the outdoor greenery and natural surroundings.
Home in Springs
4.95 out of 5 average rating, 234 reviews

Ritz-East Hampton Cottage- 5 stars

Separate 2 Bed/2 Bath guest cottage on a private family compound. Enjoy beautiful sunset views and a cool breeze located on a 5 acre waterfront property with a natural Marina, overlooks 100+ acre nature preserve. Please read the 500+ perfect reviews Superhost 43 consecutive quarters.

Popular amenities for Wainscott holiday rentals

When is the best time to visit Wainscott?

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Frequently Asked Questions

  • Are there family-friendly house rentals in Wainscott?

    Wainscott has more than 320 family-friendly house rentals. 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 house rentals in Wainscott?

    Four-legged friends are welcome in Wainscott. Choose from more than 150 house rentals for guests traveling with pets.

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

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

  • Are there Wainscott house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 300 house rentals 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 2,190 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 320 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 340 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 holiday rentals in Wainscott

  • Total holiday rentals

    Explore 380 holiday rentals in Wainscott

  • Nightly prices starting at

    Wainscott holiday rentals start at £75 per night before taxes and fees

  • Verified guest reviews

    Over 5,860 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 170 rentals that welcome pets

  • Holiday rentals with a pool

    320 properties feature pools

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

  • Wifi availability

    370 of Wainscott holiday rentals include wifi 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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