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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
The price is ¥239,399
¥312,509 total
includes taxes & fees
Jun 15 - Jun 16
Cozy 5 Bedroom With Wi-fi And Air Condition

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (23 reviews)
"Great stay & great staff!"
United States
James
The price is ¥43,225
¥49,385 total
includes taxes & fees
Jun 15 - Jun 16
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (256 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is ¥29,800
¥41,010 total
includes taxes & fees
Jun 15 - Jun 16
Cliffside Resort Condominiums

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,357 reviews)
"Had a wonderful stay"
United States
Meghan
The price is ¥74,271
¥87,992 total
includes taxes & fees
Jul 14 - Jul 15
Montauk Manor

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
The price is ¥51,024
¥62,651 total
includes taxes & fees
Jun 15 - Jun 16
Windward Shores Ocean Resort

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is ¥18,107
¥191,983 total
includes taxes & fees
Jun 16 - Jun 17
Black Swan Beachfront Home with Jacuzzi year round

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (241 reviews)
"Very close to beach"
United States
Rabia
The price is ¥51,891
¥64,505 total
includes taxes & fees
Jun 22 - Jun 23
Driftwood Resort

Town walking distance-Bridgehampton Cottage

Town walking distance-Bridgehampton Cottage
Bridgehampton
9.4 out of 10, Exceptional, (10 reviews)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
United States
Jim M.
The price is ¥198,177
¥289,945 total
includes taxes & fees
Jun 19 - Jun 20
Town walking distance-Bridgehampton Cottage

Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is ¥79,319
¥138,039 total
includes taxes & fees
Jun 17 - Jun 18
Charming Accommodations in the Hamptons

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (284 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is ¥63,095
¥80,802 total
includes taxes & fees
Jun 16 - Jun 17
The Surf Club

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (427 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is ¥34,525
¥41,189 total
includes taxes & fees
Jun 22 - Jun 23
Montauk Oceanside Suites

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is ¥346,118
¥498,394 total
includes taxes & fees
Jul 7 - Jul 8
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is ¥34,439
¥52,165 total
includes taxes & fees
Jun 23 - Jun 24
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.

US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.
Southampton
10.0 out of 10, Exceptional, (23 reviews)
"Great property as advertised!!"
United States
robert b.
The price is ¥360,540
¥579,798 total
includes taxes & fees
Jun 20 - Jun 21
US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is ¥126,357
¥219,259 total
includes taxes & fees
Jun 15 - Jun 16
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is ¥192,288
¥250,995 total
includes taxes & fees
Jun 21 - Jun 22
Cozy Hamptons Escape 3BR Minutes From Beach!

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is ¥105,598
¥138,953 total
includes taxes & fees
Jun 22 - Jun 23
Offshore Spa & Residences

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (12 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is ¥95,904
¥169,070 total
includes taxes & fees
Jun 16 - Jun 17
Beachfront Greenport Villa

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.
The price is ¥352,528
¥529,085 total
includes taxes & fees
Jul 12 - Jul 13
Brand New in the Heart of East Hampton Village with Pool
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

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:

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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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : Located near Wainscott, this vacation home rental is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

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 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.