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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Wainscott holiday rentals

Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (276 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is S$552
includes taxes & fees
6 Aug - 7 Aug
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (40 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is S$728
includes taxes & fees
24 Aug - 25 Aug
North Fork Resort
Free WiFi, individually decorated, individually furnished, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (243 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is S$636
includes taxes & fees
30 Jul - 31 Jul
Driftwood Resort
Iron/ironing board, free WiFi, individually decorated

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is S$878
includes taxes & fees
25 Aug - 26 Aug
Windward Shores Ocean Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,371 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is S$710
includes taxes & fees
3 Aug - 4 Aug
Montauk Manor
Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (436 reviews)
"The location is amazing, and the customer service is excellent. Unfortunately, the mattress and the air conditioning were the worst I’ve ever experienced, which made my stay much less comfortable."
United States
Carlos
The price is S$591
includes taxes & fees
30 Jul - 31 Jul
Montauk Oceanside Suites
Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (287 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is S$1,125
includes taxes & fees
30 Jul - 31 Jul
The Surf Club
Interior

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
The price is S$2,206
includes taxes & fees
5 Aug - 6 Aug
Hamptons Vacation Rental w/ Saltwater Pool
Living area

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
United States
Frank
The price is S$1,457
includes taxes & fees
3 Aug - 4 Aug
Offshore Spa & Residences
Living area

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
The price is S$13,310
includes taxes & fees
31 Jul - 1 Aug
Atlantic Bluffs Club
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
"Great location. Close to beach and shops"
Spencer 2-night trip
Posted less than an hour ago
Aqualina Inn Montauk

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.

How many holiday rentals are there in Wainscott?

Expedia has 37 holiday rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, 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.