Wainscott Vacation Rentals

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Our top choices for Wainscott vacation rentals

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
$172 nightly
The price is $197
Apr 30 - May 1
Total with taxes and fees
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,333 reviews)
"Incredible place to stay "
United States
melissa
$168 nightly
The price is $192
May 18 - May 19
Total with taxes and fees
Montauk Manor

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
$186 nightly
The price is $213
May 13 - May 14
Total with taxes and fees
North Fork Cottages & RV Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
$224 nightly
The price is $256
May 11 - May 12
Total with taxes and fees
Cliffside Resort Condominiums

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
$147 nightly
The price is $168
Apr 30 - May 1
Total with taxes and fees
Montauk Oceanside Suites

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
$182 nightly
The price is $208
May 25 - May 26
Total with taxes and fees
Driftwood Resort

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
$234 nightly
The price is $267
May 11 - May 12
Total with taxes and fees
The Surf Club

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
$627 nightly
The price is $716
May 3 - May 4
Total with taxes and fees
Offshore 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 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Wainscott in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $168 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home rental near Wainscott offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Wainscott?

Expedia has 40 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.