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

Wainscott Vacation Rentals

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Our top choices for Wainscott vacation rentals

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (29 reviews)
"Great stay & great staff!"
United States
James
The price is CA $487
CA $556 total
includes taxes & fees
Jul 20 - Jul 21
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 CA $579
CA $723 total
includes taxes & fees
Jul 21 - Jul 22
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 CA $759
CA $906 total
includes taxes & fees
Jul 12 - Jul 13
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 CA $658
CA $780 total
includes taxes & fees
Jul 21 - Jul 22
Montauk Manor

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 CA $817
CA $1,043 total
includes taxes & fees
Jul 8 - Jul 9
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 CA $603
CA $735 total
includes taxes & fees
Aug 5 - Aug 6
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 CA $596
CA $696 total
includes taxes & fees
Jul 16 - Jul 17
Montauk Oceanside Suites

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 CA $1,449
CA $1,818 total
includes taxes & fees
Jul 21 - Jul 22
Offshore Spa & Residences

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
The price is CA $1,602
CA $2,426 total
includes taxes & fees
Aug 5 - Aug 6
Hamptons Vacation Rental w/ Saltwater Pool

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
The price is CA $12,783
CA $14,640 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.
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Top Wainscott Hotel Reviews

Find out more about Wainscott

Everything you need to know about Wainscott vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wainscott vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wainscott vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wainscott vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wainscott vacation rentals we have selected for you start as low as CA $556 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wainscott rentals

At Expedia, we put the best Wainscott vacation 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 vacation.

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 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.

What's the top vacation rental that Wainscott has to offer?

Exquisite New Hampton Home in a Perfect Location: This vacation home near Wainscott is located by the ocean and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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.