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

Wainscott Holiday Rentals

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Our top choices for Wainscott holiday rentals

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (28 reviews)
"Great stay & great staff!"
United States
James
The price is AU$571
includes taxes & fees
13 July - 14 July
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (266 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is AU$736
includes taxes & fees
13 July - 14 July
Cliffside Resort Condominiums

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 AU$1,286
includes taxes & fees
26 July - 27 July
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,364 reviews)
"Had a wonderful stay"
United States
Meghan
The price is AU$791
includes taxes & fees
20 July - 21 July
Montauk Manor

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (286 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is AU$665
includes taxes & fees
7 July - 8 July
The Surf Club

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 AU$598
includes taxes & fees
7 July - 8 July
Driftwood Resort

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (431 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
The price is AU$632
includes taxes & fees
14 July - 15 July
Montauk Oceanside Suites

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (2 reviews)
"⭐⭐⭐⭐⭐ We had such a wonderful stay at Offshore Montauk! The hotel is beautifully designed, incredibly clean, and the location couldn’t be better—just steps from the beach and an easy walk to Montauk’s restaurants and shops. The rooms are stylish, comfortable, and so peaceful. We especially loved the pool, sauna, and cold plunge—they were the perfect way to relax and recharge after a day at the beach. Most importantly, the staff was genuinely welcoming and made us feel at home from the moment we...
United States
Iryna
The price is AU$1,844
includes taxes & fees
20 July - 21 July
Offshore Spa & Residences

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
Hamptons Vacation Rental w/ Saltwater Pool

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
The price is AU$14,851
includes taxes & fees
31 July - 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

Find out more about Wainscott

Everything you need to know about Wainscott holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wainscott holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wainscott holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wainscott holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wainscott. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wainscott holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wainscott holiday rentals we have selected for you start as low as AU$571 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wainscott rentals

At Expedia, we put the best Wainscott holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wainscott rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wainscott holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wainscott. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Exquisite New Hampton Home in a Perfect Location: This holiday home rental outside of Wainscott is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Wainscott?

Expedia has 38 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.