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Wainscott Vacation Rentals

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Our top choices for Wainscott vacation rentals

$1,699 nightly
The price is $1,941
Dec 28 - Dec 29
Total with taxes and fees
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
$156 nightly
The price is $178
Jan 12 - Jan 13, 2026
Total with taxes and fees
Montauk Manor
10.0 out of 10, Exceptional, (1)
$387 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$391 nightly
The price is $447
Jan 20 - Jan 21, 2026
Total with taxes and fees
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.
$1,114 nightly
The price is $1,273
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Condo in Downtown Montauk

Offshore Residences
4.5 star property
$579 nightly
The price is $662
Dec 28 - Dec 29
Total with taxes and fees
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.
$492 nightly
The price is $562
Jan 7 - Jan 8, 2026
Total with taxes and fees
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.
$799 nightly
The price is $913
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$691 nightly
The price is $774
Jan 14 - Jan 15, 2026
Total with taxes and fees
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.
$405 nightly
The price is $462
Dec 28 - Dec 29
Total with taxes and fees
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.
$562 nightly
The price is $642
Dec 28 - Dec 29
Total with taxes and fees
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.
$556 nightly
The price is $635
Dec 28 - Dec 29
Total with taxes and fees
Northfork Townhouse- walk to all/ newly renovated

Vacation 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.
$562 nightly
The price is $642
Dec 28 - Dec 29
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$265 nightly
The price is $303
Dec 29 - Dec 30
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
10.0 out of 10, Exceptional, (1)
$1,323 nightly
The price is $1,482
Jan 27 - Jan 28, 2026
Total with taxes and fees
My Humble Abode 2BR Beachside Home | TennisPoolPKG
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
$738 nightly
The price is $843
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$1,085 nightly
The price is $1,240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Vacation Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Dec 29 - Dec 30
Total with taxes and fees
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 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 $178 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?

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

How many vacation rentals are there in Wainscott?

Expedia has 37 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.