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

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
$1,707 nightly
The price is $1,950
Jun 23 - Jun 24
Total with taxes and fees
Cozy 5 Bedroom With Wi-fi And Air Condition

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (285 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
$366 nightly
The price is $419
Jun 24 - Jun 25
Total with taxes and fees
The Surf Club

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (430 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
$247 nightly
The price is $282
Jun 23 - Jun 24
Total with taxes and fees
Montauk Oceanside Suites

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
$738 nightly
The price is $843
Jun 23 - Jun 24
Total with taxes and fees
Offshore Spa & Residences

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk
9.6 out of 10, Exceptional, (46 reviews)
"We thoroughly enjoyed our stay. It was a great home base for exploring the area. We were able to stay nice and cozy when a snow storm hit the area as well. "
United States
Lauren B.
$602 nightly
The price is $688
Jun 26 - Jun 27
Total with taxes and fees
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,358 reviews)
"Had a wonderful stay"
United States
Meghan
$422 nightly
The price is $482
Jun 25 - Jun 26
Total with taxes and fees
Montauk Manor

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (241 reviews)
"Very close to beach"
United States
Rabia
$363 nightly
The price is $415
Jun 23 - Jun 24
Total with taxes and fees
Driftwood Resort

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (316 reviews)
"Nice homey room"
United States
Andrew
$287 nightly
The price is $328
Jun 25 - Jun 26
Total with taxes and fees
Windward Shores Ocean Resort

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge
Napeague
$818 nightly
The price is $929
Jun 30 - Jul 1
Total with taxes and fees
Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
$871 nightly
The price is $989
Jun 28 - Jun 29
Total with taxes and fees
Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"We love everything about this place. This was our 2nd time staying here and plan on coming back. The kitchen was redone and is beautiful. The location is perfect. It's close to the restaurants and shops in Montauk and Amagansett. The back deck is so roomy and comfortable. Sitting out there, listening to the ocean is heaven. We highly recommend this. "
United States
DiAnn E.
$1,015 nightly
The price is $1,153
Jul 2 - Jul 3
Total with taxes and fees
Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"First time in the area, and we hope to return. "
United States
Amy E.
$871 nightly
The price is $989
Jun 24 - Jun 25
Total with taxes and fees
Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle

Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle
Napeague
10.0 out of 10, Exceptional, (1 review)
$1,570 nightly
The price is $1,782
Jul 19 - Jul 20
Total with taxes and fees
Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
$989 nightly
The price is $1,052
Jun 28 - Jun 29
Total with taxes and fees
BlackBerry Private home with jacuzzi yearlong

Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
$1,194 nightly
The price is $1,364
Jun 24 - Jun 25
Total with taxes and fees
Spacious house in East Hampton with heated pool + WFH

Brand New in the Heart of East Hampton Village with Pool

Brand New in the Heart of East Hampton Village with Pool
East Hampton
10.0 out of 10, Exceptional, (34 reviews)
"Great location and house was spotless! "
United States
Heather R.
$3,027 nightly
The price is $3,458
Jul 12 - Jul 13
Total with taxes and fees
Brand New in the Heart of East Hampton Village with Pool

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
$259 nightly
The price is $296
Jun 23 - Jun 24
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
$259 nightly
The price is $296
Jun 23 - Jun 24
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
$295 nightly
The price is $337
Jun 28 - Jun 29
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
$537 nightly
The price is $614
Jun 23 - Jun 24
Total with taxes and fees
Lovely studio with AC in charming Sag Harbor
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 $282 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.

Explore a world of travel with Expedia

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?

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.: This vacation home near Wainscott offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a stovetop can make your vacation run smoothly.

How many vacation rentals are there in Wainscott?

Expedia has 39 vacation rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as East End Seaport Maritime Museum, 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.