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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Wainscott vacation rentals

Living area

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.
$1,268 nightly
The price is $1,351
Sep 16 - Sep 17
Total with taxes and fees
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
Property grounds

2. 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.
$514 nightly
The price is $587
Sep 20 - Sep 21
Total with taxes and fees
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Private kitchen

3. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$469 nightly
The price is $536
Sep 7 - Sep 8
Total with taxes and fees
Charming Accommodations in the Hamptons
Room

4. 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
$232 nightly
The price is $266
Sep 27 - Sep 28
Total with taxes and fees
Windward Shores Ocean Resort
Condo | Terrace/patio

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (289 reviews)
"Great place!"
United States
Christine
$380 nightly
The price is $434
Sep 21 - Sep 22
Total with taxes and fees
Cliffside Resort Condominiums
Living area

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (51 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$286 nightly
The price is $326
Sep 7 - Sep 8
Total with taxes and fees
North Fork Resort
Property grounds

7. 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 31 - Sep 1
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Living area

8. Beautiful East Hampton Retreat

Beautiful East Hampton Retreat
East Hampton
9.6 out of 10, Exceptional, (5 reviews)
"Great home and had all the amenities we needed and good location! Really responsive host also. "
United States
Neeraj P.
$1,194 nightly
The price is $1,364
Aug 31 - Sep 1
Total with taxes and fees
Beautiful East Hampton Retreat
Apartment

9. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (248 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
$195 nightly
The price is $223
Sep 21 - Sep 22
Total with taxes and fees
Driftwood Resort
Pool

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

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
$1,071 nightly
The price is $1,224
Sep 1 - Sep 2
Total with taxes and fees
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Property grounds

11. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"great"
United States
Fiona B.
$270 nightly
The price is $309
Aug 31 - Sep 1
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
Exterior

12. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
$537 nightly
The price is $614
Sep 13 - Sep 14
Total with taxes and fees
Lovely studio with AC in charming Sag Harbor
Lobby

13. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,395 reviews)
"Beautiful property"
United States
John
$314 nightly
The price is $359
Sep 14 - Sep 15
Total with taxes and fees
Montauk Manor
Dining

14. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"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.
$1,586 nightly
The price is $1,696
Sep 8 - Sep 9
Total with taxes and fees
BlackBerry Private home with jacuzzi yearlong
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, (10 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,D29-CedarPt, East Hampton, NY

Safari Tent Glamping,D29-CedarPt, East Hampton, NY
East Hampton
8.0 out of 10, Very Good, (1 review)
"If you upgrade the bathroom and shower facilities for glamping only- even if you increase the rate to stay- that would make it a true glamping experience. Willing to pay extra for better bathrooms and showers. Consider renting fancy bathroom and showers and increasing your prices. Thank you. Other than that it was wonderful."
United States
Aurelia
$270 nightly
The price is $309
Aug 31 - Sep 1
Total with taxes and fees
Safari Tent Glamping,D29-CedarPt, East Hampton, NY
Private kitchen

17. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Great clean beautiful property."
United States
ANGELA S.
$1,027 nightly
The price is $1,173
Sep 27 - Sep 28
Total with taxes and fees
Spacious house in East Hampton with heated pool + WFH
Private kitchen

18. 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.
$1,151 nightly
The price is $1,315
Sep 23 - Sep 24
Total with taxes and fees
Work and Play Special! Extended Stay Discount
Exterior

19. Unit 2024: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side

Unit 2024: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side
Napeague
$778 nightly
The price is $884
Sep 1 - Sep 2
Total with taxes and fees
Unit 2024: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side
Property grounds

20. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
$259 nightly
The price is $296
Aug 31 - Sep 1
Total with taxes and fees
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Loved the location!"
Jessica 1-night trip
Posted 11 hours ago
Sound View Greenport

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 $205 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 Children's Museum of The East End, 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.