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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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Home in East Hampton

5.0 out of 5 average rating, 18 reviews

Renovated 1800s Modern Farmhouse - House A

Newly Renovated 1800s Scandinavian-Modern Farmhouse in East Hampton Village. LEFT SIDE HOME in a Legal 2 family home; PRIVATE open plan kitchen, living room, 3 bedrooms, each with en-suite bathroom and TV, and light-filled finished lower level with Media Room and additional recreational/office space, powder room and laundry room. Set upon a verdant front and backyard (7/10th acre) shared with the Right Side Home. Sidewalks take you to all East Hampton Village and only 1.5 miles to ocean beaches.

Guest favourite

Apartment in Sagaponack

4.97 out of 5 average rating, 38 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.

Jun. 2 – 9

$733 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 29 reviews

Storybook Cottage Seconds to East Hampton Village

Beach Cottage at edge of East Hampton Village. This fresh and bright cottage with three bedrooms and two new bathrooms is a compact and convenient jewel box with everything you'd expect in the Hamptons - including a beautiful pool with built-in hot tub. Just blocks from the heart of East Hampton on a quiet no-traffic cul-de-sac, not far from beach, shopping, dining and train... sparkling kitchen with new 'retro style' appliances, gleaming hardwood floors throughout, and a cozy front porch.

Oct. 23 – 30

$780 CAD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 119 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.

Dec. 23 – 30

$999 CAD per night

Guest favourite

Guest suite in East Hampton

4.96 out of 5 average rating, 142 reviews

Private peaceful poolside Suite close to bch/town

Beautiful, bright, spacious king suite w fireplace, two bathrooms & private separate poolside entrance in the country. We are just minutes to golf, hiking, biking, yoga, wineries and beaches. Play games, grill poolside 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/snacks and breakfast treats provided.

Jun. 20 – 27

$853 CAD per night

Guest favourite

Apartment in Sag Harbor

4.98 out of 5 average rating, 131 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!

Oct. 3 – 10

$500 CAD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Oct. 2 – 9

$1,313 CAD per night

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

Oct. 28 – Nov. 4

$599 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 20 reviews

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Nov. 3 – 10

$502 CAD per night

Guest favourite

Apartment in Sag Harbor

4.88 out of 5 average rating, 133 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic.

Oct. 30 – Nov. 6

$367 CAD per night

Guest favourite

Cottage in East Hampton

4.98 out of 5 average rating, 263 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).

Nov. 5 – 12

$445 CAD per night

Guest favourite

Apartment in East Hampton

4.98 out of 5 average rating, 80 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 .

Oct. 23 – 30

$574 CAD per night

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Popular amenities for Wainscott vacation rentals

Free parking on premises

Air conditioning

Stay near Wainscott's top sights

Townline BBQ36 locals recommend

La Capannina12 locals recommend

The Wine Stand at Wölffer Estate25 locals recommend

Levain Bakery - Wainscott21 locals recommend

The Clubhouse45 locals recommend

HomeGoods4 locals recommend

Other great vacation rentals in Wainscott

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

East hampton 3 bedroom home w/ pool great location

Nov. 14 – 21

$651 CAD per night

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Historic East Hampton Home - Private Beach Access

Feb. 5 – 12

$825 CAD per night

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 16 reviews

Stunning 3 BR / 2.5 New Construction with Pool

Oct. 9 – 16

$1,470 CAD per night

Home in Sagaponack

4.87 out of 5 average rating, 45 reviews

Nature Retreat

Feb. 18 – 25

$1,309 CAD per night

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 14 reviews

Cozy Beach Oasis in East Hampton + Pool

Oct. 2 – 9

$1,280 CAD per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 92 reviews

Secluded Modern Beach Style House

Sep. 1 – 8

$1,199 CAD per night

Home in East Hampton

4.97 out of 5 average rating, 69 reviews

Stylish Artist's Home in EH 4B, Pool, Paradise

Sep. 29 – Oct. 6

$1,584 CAD per night

Guest favourite

Home in East Hampton

4.94 out of 5 average rating, 87 reviews

Marvelous 4 Bed East Hampton home w Heated Pool

Sep. 24 – Oct. 1

$1,589 CAD per night

Quick stats about vacation rentals in Wainscott

Total rentals
280 properties
Rentals with a pool
230 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
250 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
$69 CAD before taxes and fees

Destinations to explore