A coastal landscape with a beach, ocean waves, and a sunset sky.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Wainscott holiday rentals

A kitchen with a central island, white cabinetry, and a brick accent wall.

1. !! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
Wainscott
10.0 out of 10, Exceptional, (33 reviews)
"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "
United States
Leigh E.
The price is £1,704
includes taxes & fees
4 Oct - 5 Oct
!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

2. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (3 reviews)
"This house is absolutely wonderful and in a great location. It is beautifully decorated and the grounds are immaculate. The host has paid close attention to detail; everything we could ever need was there! We loved our stay, highly highly recommend ....."
United States
Carolyn C.
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

3. 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, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is £484
includes taxes & fees
13 Oct - 14 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A small cabin with a porch, surrounded by trees and a fenced area.

4. 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 £406
includes taxes & fees
27 Sept - 28 Sept
Lovely studio with AC in charming Sag Harbor
A tent with a wooden frame, two red chairs, and a table.

5. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is £250
includes taxes & fees
2 Oct - 3 Oct
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (294 reviews)
"Great place!"
United States
Christine
The price is £287
includes taxes & fees
25 Oct - 26 Oct
Cliffside Resort Condominiums
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

7. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is £1,646
includes taxes & fees
27 Sept - 28 Sept
Lovely & Spacious Sag Harbor escape with heated pool
A tented accommodation with a bed, a small table, and a chair.

8. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Outstanding place"
United States
Michael H.
The price is £250
includes taxes & fees
2 Oct - 3 Oct
Safari Tent Glamping,S2-CedarPt, East Hampton, NY
A rectangular swimming pool with a pebble border and a fire feature in the center.

9. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
The price is £695
includes taxes & fees
8 Oct - 9 Oct
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
A modern house with a deck, outdoor seating, and a fire pit.

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (58 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is £220
includes taxes & fees
26 Oct - 27 Oct
North Fork Resort
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

11. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
The price is £980
includes taxes & fees
27 Sept - 28 Sept
Work and Play Special! Extended Stay Discount
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

12. 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 £842
includes taxes & fees
27 Sept - 28 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

13. Unit 511: Cottage | Ocean View | Nautilus

Unit 511: Cottage | Ocean View | Nautilus
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
The price is £754
includes taxes & fees
26 Oct - 27 Oct
Unit 511: Cottage | Ocean View | Nautilus
A covered patio with a table and chairs, large windows, and a view of greenery.

14. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is £444
includes taxes & fees
27 Sept - 28 Sept
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

15. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
The price is £1,973
includes taxes & fees
30 Sept - 1 Oct
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

16. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (251 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is £151
includes taxes & fees
4 Oct - 5 Oct
Driftwood Resort
A modern living room with a blue sofa, a wooden coffee table, and a kitchen area with cabinets and a countertop.

17. Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this property! Very clean, just steps to the beach and close to everything we love in the Hamptons!"
United States
Pamela
The price is £420
includes taxes & fees
27 Sept - 28 Sept
Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

18. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is £405
includes taxes & fees
27 Sept - 28 Sept
Charming Accommodations in the Hamptons
A campground with several tents and trees, a grassy area, and a view of the water.

19. Safari Tent Glamping,S3-CedarPt, East Hampton, NY

Safari Tent Glamping,S3-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"The store was great and the upgrades were perfect. The pizza was excellent and hope to be back soon"
United States
Joseph
The price is £250
includes taxes & fees
2 Oct - 3 Oct
Safari Tent Glamping,S3-CedarPt, East Hampton, NY
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 Hotel Reviews

Zey Hotel

Zey Hotel

8/10 Good
"We got off the Orient Point ferry late in evening and were welcomed so warmly by the host! Its like stepping back to a lovely time with the cozy living room on 2 floors and elegant furnishings. The complimentary coffee and lemon water. We loved the cozy feel of the living room that we just picked up muffins from a bakery and ate them with the coffee there. The ONLY reason we gave 4 stars, not 5 is the room had no sound barrier abd we heard next door t.v. on til almost midnight. We loved our stay other than that.0"
alison g 1-night trip
Posted 1 hour ago
Zey Hotel

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Frequently asked questions

Can I find holiday rentals in Wainscott?

Yes, there are holiday rentals close to the most popular sights in Wainscott, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Wainscott. Make sure you have time to check out the bars and coffee shops during your trip.

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

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Wainscott is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 holiday rentals are there in Wainscott?

Expedia has 38 holiday rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as East End Seaport Maritime Museum, or get out into nature at a spot like The Hamptons Beaches. In the wider area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are holiday rentals like in Wainscott?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wainscott. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family getaway.