Holiday Rentals in Wainscott

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Our top choices for Wainscott holiday rentals

The price is €1,697
includes taxes & fees
9 Jan - 10 Jan 2026
Cozy 5 Bedroom With Wi-fi And Air Condition

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1273)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is €151
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
10.0 out of 10, Exceptional, (1)
The price is €382
includes taxes & fees
4 Jan - 5 Jan 2026
Seabreeze #3: Cozy Cottage by the beach
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
The price is €387
includes taxes & fees
20 Jan - 21 Jan 2026
Seabreeze #4: Charming Cottage Footsteps to the Beach
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is €1,107
includes taxes & fees
1 Jan - 2 Jan 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is €1,106
includes taxes & fees
5 Jan - 6 Jan 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Condo in Downtown Montauk

Offshore Residences
4.5 star property
The price is €561
includes taxes & fees
8 Jan - 9 Jan 2026
Offshore Residences
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is €505
includes taxes & fees
7 Jan - 8 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
9.0 out of 10, Wonderful, (4)
"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.
The price is €794
includes taxes & fees
20 Jan - 21 Jan 2026
Blackberry: Private home with jacuzzi year-round
10.0 out of 10, Exceptional, (1)
"Great stay. Unfortunately, they told us there was pickleball but there wasn’t. "
United States
Kevin C.
The price is €673
includes taxes & fees
14 Jan - 15 Jan 2026
Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub
2.5 star property
9.6 out of 10, Exceptional, (16)
"Wonderful & perfect for my pup and I. I’d go back!"
United States
Scott C.
The price is €402
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is €587
includes taxes & fees
28 Dec - 29 Dec
Charming Northfork Townhouse- walk to all
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is €553
includes taxes & fees
28 Dec - 29 Dec
Northfork Townhouse- walk to all/ newly renovated

Holiday Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is €558
includes taxes & fees
28 Dec - 29 Dec
Immaculate Waterfront 2 bedroom!
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €251
includes taxes & fees
20 Jan - 21 Jan 2026
American Beech in Greenport - Petite King Room 7
10.0 out of 10, Exceptional, (1)
The price is €1,291
includes taxes & fees
27 Jan - 28 Jan 2026
My Humble Abode 2BR Beachside Home | TennisPoolPKG
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is €965
includes taxes & fees
28 Dec - 29 Dec
Minutes from the beach, brand new 4 bedroom
9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is €778
includes taxes & fees
4 Jan - 5 Jan 2026
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
9.4 out of 10, Exceptional, (3)
"Wonderful property. Lisette was a fantastic host and her home updated and modern. "
United States
Joanna D.
The price is €1,079
includes taxes & fees
31 Dec - 1 Jan 2026
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Holiday Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is €1,022
includes taxes & fees
29 Dec - 30 Dec
Beautifully farmhouse
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 holiday rentals

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

Wainscott holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wainscott holiday rentals we have selected for you start as low as €151 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 holiday 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 holiday.

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 holiday rentals in Wainscott?

Yes, there are holiday rentals close to the most popular sights in Wainscott, or you can select a more 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 coffee shops during your trip.

What are some of the best holiday rentals that Wainscott has to offer?

Stunning Hampton Holiday Family Fantasy for your Team : This holiday home rental outside of Wainscott is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Wainscott?

Expedia has 37 holiday 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 wider area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are holiday rentals like in Wainscott?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wainscott. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family getaway.