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

Wainscott Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Wainscott vacation rentals

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (294 reviews)
"Great place!"
United States
Christine
The price is P14,738
P23,770 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (58 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is P17,037
P19,465 total
includes taxes & fees
Oct 25 - Oct 26
North Fork Resort

3. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is P7,431
P10,189 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (251 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is P9,179
P12,523 total
includes taxes & fees
Oct 4 - Oct 5
Driftwood Resort
A spacious hallway with high ceilings, arched columns, and chandeliers.

5. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,407 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is P8,059
P10,431 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (452 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is P7,380
P9,111 total
includes taxes & fees
Oct 20 - Oct 21
Montauk Oceanside Suites
A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.

7. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 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 P34,805
P43,333 total
includes taxes & fees
Oct 4 - Oct 5
Offshore Spa & Residences

8. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (302 reviews)
"Found mold under the pull-out couch"
United States
Anna
The price is P14,057
P20,019 total
includes taxes & fees
Oct 7 - Oct 8
The Surf 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

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Bathroom in my unit was kind of outdated but still adequate Seen another unit and it was updated beautifully"
John 2-night trip
Posted 3 hours ago
Ocean Surf Resort

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.

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 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.