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

Our top choices for Wainscott Woods vacation rentals

Room

1. 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 ￥22,041
￥29,478 total
includes taxes & fees
Oct 25 - Oct 26
Windward Shores Ocean Resort
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (68 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ￥46,259
￥52,849 total
includes taxes & fees
Oct 21 - Oct 22
North Fork Resort
Room

3. 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 ￥21,647
￥29,878 total
includes taxes & fees
Oct 25 - Oct 26
Driftwood Resort
Terrace/patio

4. 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 ￥26,791
￥48,195 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
A spacious hallway with high ceilings, arched columns, and chandeliers.

5. 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 ￥23,168
￥29,574 total
includes taxes & fees
Nov 17 - Nov 18
Montauk Manor
Room

6. 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 ￥22,399
￥27,310 total
includes taxes & fees
Oct 25 - Oct 26
Montauk Oceanside Suites
Living area

7. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
United States
na
The price is ￥34,650
￥49,591 total
includes taxes & fees
Nov 10 - Nov 11
The Surf Club
A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.

8. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 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 ￥57,782
￥75,073 total
includes taxes & fees
Nov 1 - Nov 2
Offshore Spa & Residences
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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 14 hours ago
The Atlantic Hotel

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:

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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.