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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Wainscott Woods holiday rentals

Room

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (332 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 ฿4,409
฿5,947 total
includes taxes & fees
9 Nov - 10 Nov
Windward Shores Ocean Resort
A spacious hallway with high ceilings, arched columns, and chandeliers.

2. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,420 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is ฿4,638
฿5,954 total
includes taxes & fees
30 Nov - 1 Dec
Montauk Manor
A balcony with a view of the ocean, a lawn, and a house in the background.

3. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ฿5,772
฿10,319 total
includes taxes & fees
30 Nov - 1 Dec
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

4. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ฿10,752
฿12,285 total
includes taxes & fees
11 Nov - 12 Nov
North Fork Resort
Room

5. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (460 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
The price is ฿4,554
฿5,567 total
includes taxes & fees
9 Nov - 10 Nov
Montauk Oceanside Suites
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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Find holiday rentals that suit your style

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Top Wainscott Woods Hotel Reviews

A beach with waves gently lapping onto the shore.
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North

10/10 Excellent

V
United Kingdom
Mark
Reviewed June 11, 2025
The Roundtree, Amagansett

Find out more about Wainscott Woods

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

  • View our selection of featured holiday rentals in Wainscott Woods
  • Use the map to find apartments and other holiday homes in the Wainscott Woods neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wainscott Woods while they last

Look no further and take a look at our great range of rental properties in Wainscott Woods!

Frequently Asked Questions

Can I find a holiday rental in Wainscott Woods?

Yes, there are holiday rentals close to the most popular sights in Wainscott Woods, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Wainscott Woods?

With 19 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Wainscott Woods like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wainscott Woods. Holiday rentals offer amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.