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

Wainscott Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Wainscott vacation rentals

TV, fireplace, books, stereo

1. 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
10.0 out of 10, Exceptional, (2 reviews)
"We have just returned from an amazing summer experience in East Hampton! From the minute I secured the booking to checkout, everything was perfectly smooth! The house was so wonderful, every design detail and amenity…. It was truly like the best of all possible creature comforts…. Fully stocked kitchen, incredible fire pit for late evening s’mores, extraordinary huge pool, patio with outdoor speakers, and enough indoor space meticulously designed and decorated that proved our dream vacation...
United States
GINA W.
$1,443 nightly
The price is $1,538
Sep 16 - Sep 17
Total with taxes and fees
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
Coffee/tea maker, fridge, microwave, oven

2. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$754 nightly
The price is $861
Aug 18 - Aug 19
Total with taxes and fees
Charming Accommodations in the Hamptons
Property grounds

3. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
$525 nightly
The price is $599
Sep 13 - Sep 14
Total with taxes and fees
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Condo | Terrace/patio

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (284 reviews)
"Great place!"
United States
Christine
$385 nightly
The price is $439
Sep 7 - Sep 8
Total with taxes and fees
Cliffside Resort Condominiums
Interior

5. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
$1,255 nightly
The price is $1,434
Sep 13 - Sep 14
Total with taxes and fees
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Flat-screen TV

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$275 nightly
The price is $314
Sep 13 - Sep 14
Total with taxes and fees
North Fork Resort
Terrace/patio

7. Safari Tent Glamping,S11-CedarPt, East Hampton, NY

Safari Tent Glamping,S11-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Our tent was spacious and the bed was very comfortable with an incredible view of the harbor. Dave and Lee were very gracious and helpful. We especially enjoyed the Camp Store and the delicious omelets. Plus - how quiet and peaceful it was!"
United States
Lee
$259 nightly
The price is $296
Aug 18 - Aug 19
Total with taxes and fees
Safari Tent Glamping,S11-CedarPt, East Hampton, NY
Property grounds

8. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Comfortable bed and beautiful surroundings"
United States
Matthew
$259 nightly
The price is $296
Aug 18 - Aug 19
Total with taxes and fees
Safari Tent Glamping,S2-CedarPt, East Hampton, NY
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
$259 nightly
The price is $296
Aug 20 - Aug 21
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Iron/ironing board, WiFi (free), individually decorated

10. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 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
$265 nightly
The price is $303
Sep 14 - Sep 15
Total with taxes and fees
Windward Shores Ocean Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

11. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (246 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
$263 nightly
The price is $300
Sep 13 - Sep 14
Total with taxes and fees
Driftwood Resort
Exterior

12. Unit 823: Studio | 2nd Floor-Ocean View | Osprey

Unit 823: Studio | 2nd Floor-Ocean View | Osprey
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"Loved having coffe on the deck enjoying the views. The location was perfect for us. Hope to be back!"
United States
Dianna L.
$705 nightly
The price is $801
Aug 18 - Aug 19
Total with taxes and fees
Unit 823: Studio | 2nd Floor-Ocean View | Osprey
Coffee/tea maker, fridge, microwave, oven

13. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
$1,202 nightly
The price is $1,374
Sep 15 - Sep 16
Total with taxes and fees
Work and Play Special! Extended Stay Discount
Lobby

14. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,387 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
$314 nightly
The price is $359
Sep 7 - Sep 8
Total with taxes and fees
Montauk Manor
Outdoor dining

15. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (9 reviews)
"great experience"
United States
Jordan
$514 nightly
The price is $587
Aug 31 - Sep 1
Total with taxes and fees
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Property grounds

16. 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
Aug 18 - Aug 19
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
Living area

17. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
$1,251 nightly
The price is $1,429
Sep 7 - Sep 8
Total with taxes and fees
Minutes from the beach, brand new 3 bedroom
Exterior

18. Safari Tent Glamping,D26-CedarPt, East Hampton, NY

Safari Tent Glamping,D26-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"This campground is a pleasant and relaxing place to spend a few days. I love to sit by the fire pit and look out on the water. The new on site pizza place was delicious."
United States
Melissa
$295 nightly
The price is $337
Aug 25 - Aug 26
Total with taxes and fees
Safari Tent Glamping,D26-CedarPt, East Hampton, NY
Interior

19. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
$1,119 nightly
The price is $1,278
Sep 9 - Sep 10
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Beach nearby, sun loungers, beach towels

20. Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
$913 nightly
The price is $1,043
Sep 14 - Sep 15
Total with taxes and fees
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wainscott Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Best deal in Hamptons- clean renovated, charming comfortable great fur families- huge beautiful enclosed lawn- close to beaches and a complimentary beach pass for parking! They also supply umbrellas and chairs! Highly recommend"
Rebecca 2-night trip
Posted 10 hours ago
The Bentley Hotel Southampton

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 $244 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?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental near Wainscott is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 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.