A lighthouse on a rocky coastline with a clear blue sky.

Wainscott Woods Vacation Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Wainscott Woods vacation rentals

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

1. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is AED 826
AED 1,859 total
includes taxes & fees
26 Oct - 27 Oct
Charming Accommodations in the Hamptons
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

2. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is AED 1,047
AED 2,157 total
includes taxes & fees
15 Nov - 16 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Room

3. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (330 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is AED 512
AED 685 total
includes taxes & fees
25 Oct - 26 Oct
Windward Shores Ocean Resort
Room

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is AED 503
AED 694 total
includes taxes & fees
22 Oct - 23 Oct
Driftwood Resort
Terrace/patio

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is AED 621
AED 1,117 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
A small cabin with a porch, surrounded by trees and a fenced area.

6. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is AED 826
AED 1,918 total
includes taxes & fees
22 Oct - 23 Oct
Lovely studio with AC in charming Sag Harbor
A modern house with a deck, outdoor seating, and a fire pit.

7. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (69 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is AED 1,088
AED 1,243 total
includes taxes & fees
27 Oct - 28 Oct
North Fork Resort
A dining area with a round table, six chairs, and a chandelier.

8. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is AED 228
AED 4,619 total
includes taxes & fees
22 Oct - 23 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A kitchen with a central island, white cabinetry, and a brick accent wall.

9. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
United States
Suzanne B.
The price is AED 3,926
AED 8,385 total
includes taxes & fees
19 Nov - 20 Nov
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

10. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is AED 1,978
AED 4,262 total
includes taxes & fees
22 Oct - 23 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A spacious hallway with high ceilings, arched columns, and chandeliers.

11. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,417 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is AED 537
AED 685 total
includes taxes & fees
17 Nov - 18 Nov
Montauk Manor
A spacious living area with a large bed, a dining table, and a kitchen in the background.

12. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
The price is AED 591
AED 1,540 total
includes taxes & fees
22 Oct - 23 Oct
Unit 1021: Studio | 2nd Floor-Pool View | Starfish
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

13. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is AED 1,653
AED 3,932 total
includes taxes & fees
22 Oct - 23 Oct
Spacious house in East Hampton with heated pool + WFH
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

14. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is AED 628
AED 2,195 total
includes taxes & fees
25 Oct - 26 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Room

15. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (457 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is AED 521
AED 635 total
includes taxes & fees
22 Oct - 23 Oct
Montauk Oceanside Suites
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

16. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is AED 1,952
AED 4,427 total
includes taxes & fees
22 Oct - 23 Oct
Amazing Southampton Home with Private Heated Pool
A beach with people relaxing on chairs and sunbathing.

17. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is AED 314
AED 892 total
includes taxes & fees
2 Nov - 3 Nov
Harbor Heights
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

18. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is AED 1,653
AED 4,075 total
includes taxes & fees
22 Oct - 23 Oct
Minutes from the beach, brand new 4 bedroom
A wooden pathway leading to a beach with scattered rocks and greenery.

19. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AED 716
AED 1,653 total
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

20. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.8 out of 10, Excellent, (3 reviews)
"We only needed a one night stay but this place was clean and comfortable for what we needed! The beds are super comfortable."
United States
Sherry L.
The price is AED 1,109
AED 2,260 total
includes taxes & fees
22 Oct - 23 Oct
Unit 1311: Cottage | Garden View | Deuce
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wainscott Woods Hotel Reviews

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Great property and view."
Trevor 2-night trip
Posted 6 hours ago
Montauk Yacht Club

Frequently asked questions

Can I find a vacation rental in Wainscott Woods?

Yes, we have vacation rentals near the most popular attractions in Wainscott Woods, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Wainscott Woods has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Wainscott Woods is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Wainscott Woods?

With 19 Expedia vacation rentals, you're sure to find just the right place for your Wainscott Woods stay.

What’s there to see and do in Wainscott Woods?

Explore the area and family-friendly sights such as East End Seaport Maritime Museum, or get out into nature at a spot like Georgica Beach. Wolffer Estates Vineyard and The Jewish Center of the Hamptons are a couple of places you'll find in the larger area.

What’s a vacation rental in Wainscott Woods like?

A vacation rental is a private property you can stay in for a couple of days or more in Wainscott Woods. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.