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

Wainscott Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Wainscott vacation rentals

Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (273 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 NT$13,288
NT$16,587 total
includes taxes & fees
Jul 30 - Jul 31
Cliffside Resort Condominiums
Iron/ironing board, WiFi (free), 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 NT$14,022
NT$16,899 total
includes taxes & fees
Jul 23 - Jul 24
Windward Shores Ocean Resort
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (33 reviews)
"Great stay & great staff!"
United States
James
The price is NT$17,080
NT$19,514 total
includes taxes & fees
Aug 2 - Aug 3
North Fork Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (242 reviews)
"Very close to beach"
United States
Rabia
The price is NT$18,077
NT$21,707 total
includes taxes & fees
Aug 2 - Aug 3
Driftwood Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,367 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is NT$14,985
NT$17,754 total
includes taxes & fees
Aug 4 - Aug 5
Montauk Manor
Apartment | Iron/ironing board, WiFi (free)

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (435 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 NT$12,649
NT$14,803 total
includes taxes & fees
Jul 22 - Jul 23
Montauk Oceanside Suites
Apartment | 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 NT$24,744
NT$31,017 total
includes taxes & fees
Jul 23 - Jul 24
The Surf Club
Cottage (3 Bedrooms) | Interior

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
Hamptons Vacation Rental w/ Saltwater Pool
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

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 NT$31,652
NT$39,856 total
includes taxes & fees
Jul 20 - Jul 21
Offshore Spa & Residences
Premium Apartment, 1 Bedroom, Ocean View | Living area

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
The price is NT$290,950
NT$333,219 total
includes taxes & fees
Jul 31 - Aug 1
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wainscott Hotel Reviews

North Fork Resort

North Fork Resort

8/10 Good
"Would stay again. Had asked for two cabins next to each other but ended up being opposite sides of the resort. They need to pave the road through the property, the dust in the summer months is not good. Pool was lovely but there was no bar/ restaurant opened."
Laura 2-night trip
Posted 11 hours ago
North Fork Resort

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

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

Frequently asked questions

Can I find vacation rentals in Wainscott?

Yes, we have vacation rentals near well known points of interest in Wainscott, or you can choose a 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 coffeehouses during your trip.

How many vacation rentals are there in Wainscott?

Expedia has 38 vacation 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 larger area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are vacation rentals like in Wainscott?

Vacation rentals are privately owned properties you can book for a short or long stay in Wainscott. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for small groups.