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

Wainscott Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Wainscott holiday rentals

Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is HK$11,714
HK$15,292 total
includes taxes & fees
25 Jun - 26 Jun
Cozy 5 Bedroom With Wi-fi And Air Condition
Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (285 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is HK$5,411
HK$6,608 total
includes taxes & fees
5 Jul - 6 Jul
The Surf Club
Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (430 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
The price is HK$2,223
HK$2,625 total
includes taxes & fees
25 Jun - 26 Jun
Montauk Oceanside Suites
Living area

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is HK$7,519
HK$9,487 total
includes taxes & fees
25 Jun - 26 Jun
Offshore Spa & Residences
Interior

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk
9.6 out of 10, Exceptional, (47 reviews)
"We thoroughly enjoyed our stay. It was a great home base for exploring the area. We were able to stay nice and cozy when a snow storm hit the area as well. "
United States
Lauren B.
The price is HK$2,764
HK$5,397 total
includes taxes & fees
26 Jun - 27 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,359 reviews)
"Had a wonderful stay"
United States
Meghan
The price is HK$3,634
HK$4,306 total
includes taxes & fees
16 Jul - 17 Jul
Montauk Manor
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (241 reviews)
"Very close to beach"
United States
Rabia
The price is HK$2,012
HK$2,554 total
includes taxes & fees
25 Jun - 26 Jun
Driftwood Resort
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (316 reviews)
"Nice homey room"
United States
Andrew
The price is HK$2,041
HK$2,546 total
includes taxes & fees
25 Jun - 26 Jun
Windward Shores Ocean Resort
Exterior

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge
Napeague
The price is HK$4,148
HK$7,287 total
includes taxes & fees
30 Jun - 1 Jul
Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge
Exterior

Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
The price is HK$4,485
HK$7,758 total
includes taxes & fees
28 Jun - 29 Jun
Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Exterior

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"We love everything about this place. This was our 2nd time staying here and plan on coming back. The kitchen was redone and is beautiful. The location is perfect. It's close to the restaurants and shops in Montauk and Amagansett. The back deck is so roomy and comfortable. Sitting out there, listening to the ocean is heaven. We highly recommend this. "
United States
DiAnn E.
The price is HK$5,496
HK$9,155 total
includes taxes & fees
2 Jul - 3 Jul
Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West
Exterior

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"First time in the area, and we hope to return. "
United States
Amy E.
The price is HK$5,496
HK$9,155 total
includes taxes & fees
27 Jun - 28 Jun
Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Exterior

Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle

Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle
Napeague
10.0 out of 10, Exceptional, (1 review)
The price is HK$8,970
HK$13,976 total
includes taxes & fees
19 Jul - 20 Jul
Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 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 HK$886
HK$7,969 total
includes taxes & fees
28 Jun - 29 Jun
BlackBerry Private home with jacuzzi yearlong
Private kitchen

Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
The price is HK$9,273
HK$15,046 total
includes taxes & fees
6 Jul - 7 Jul
Spacious house in East Hampton with heated pool + WFH
Fridge, microwave, oven, stovetop

Brand New in the Heart of East Hampton Village with Pool

Brand New in the Heart of East Hampton Village with Pool
East Hampton
10.0 out of 10, Exceptional, (34 reviews)
"Great location and house was spotless! "
United States
Heather R.
The price is HK$17,250
HK$27,116 total
includes taxes & fees
12 Jul - 13 Jul
Brand New in the Heart of East Hampton Village with Pool
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,685
HK$2,552 total
includes taxes & fees
1 Jul - 2 Jul
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is HK$1,685
HK$2,552 total
includes taxes & fees
30 Jun - 1 Jul
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is HK$1,685
HK$2,651 total
includes taxes & fees
13 Jul - 14 Jul
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
Exterior

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
The price is HK$3,881
HK$6,861 total
includes taxes & fees
30 Jun - 1 Jul
Lovely studio with AC in charming Sag Harbor
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

Aqualina Inn Montauk

Aqualina Inn Montauk

10/10 Excellent
"It was in general a very nice stay!"
Jiawei 1-night trip
Posted 2 hours ago
Aqualina Inn Montauk

Find out more about Wainscott

Search for holiday rentals in Wainscott on Expedia! You can easily find your home rentals, villas, holiday apartments in Wainscott using one of the methods below:

  • View our selection of featured holiday rentals in Wainscott
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Look no further and take a look at our great range of rental properties in Wainscott!

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?

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.: This holiday home rental outside of Wainscott offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a stovetop can make your holiday run smoothly.

How many holiday rentals are there in Wainscott?

Expedia has 39 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.