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

A kitchen with a central island, white cabinetry, and a brick accent wall.

1. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!
Wainscott
10.0 out of 10, Exceptional, (33 reviews)
"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "
United States
Leigh E.
$1,987 nightly
The price is $2,270
Oct 4 - Oct 5
Total with taxes and fees
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

2. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (3 reviews)
"This house is absolutely wonderful and in a great location. It is beautifully decorated and the grounds are immaculate. The host has paid close attention to detail; everything we could ever need was there! We loved our stay, highly highly recommend ....."
United States
Carolyn C.
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

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.
$569 nightly
The price is $650
Oct 11 - Oct 12
Total with taxes and fees
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A small cabin with a porch, surrounded by trees and a fenced area.

4. 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.
$480 nightly
The price is $548
Sep 27 - Sep 28
Total with taxes and fees
Lovely studio with AC in charming Sag Harbor

5. 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.
$260 nightly
The price is $298
Sep 25 - Sep 26
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (294 reviews)
"Great place!"
United States
Christine
$373 nightly
The price is $427
Oct 25 - Oct 26
Total with taxes and fees
Cliffside Resort Condominiums
A compact laundry room with a washing machine, a dryer, and a small sink area.

7. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
$1,948 nightly
The price is $2,226
Sep 25 - Sep 26
Total with taxes and fees
Lovely & Spacious Sag Harbor escape with heated pool
A campground with several tents and trees, a grassy area, and a view of the water.

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, (2 reviews)
"Outstanding place"
United States
Michael H.
$260 nightly
The price is $298
Sep 25 - Sep 26
Total with taxes and fees
Safari Tent Glamping,S2-CedarPt, East Hampton, NY
A rectangular swimming pool with a pebble border and a fire feature in the center.

9. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
$890 nightly
The price is $948
Oct 8 - Oct 9
Total with taxes and fees
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
A modern house with a deck, outdoor seating, and a fire pit.

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (57 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$270 nightly
The price is $308
Oct 19 - Oct 20
Total with taxes and fees
North Fork Resort
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

11. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
$1,165 nightly
The price is $1,331
Sep 27 - Sep 28
Total with taxes and fees
Work and Play Special! Extended Stay Discount
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

12. 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.
$975 nightly
The price is $1,114
Sep 25 - Sep 26
Total with taxes and fees
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

13. Unit 511: Cottage | Ocean View | Nautilus

Unit 511: Cottage | Ocean View | Nautilus
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
$897 nightly
The price is $1,018
Oct 4 - Oct 5
Total with taxes and fees
Unit 511: Cottage | Ocean View | Nautilus
A covered patio with a table and chairs, large windows, and a view of greenery.

14. 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)
"Very nice place and super responsive host. "
United States
Angelo D.
$514 nightly
The price is $587
Sep 27 - Sep 28
Total with taxes and fees
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

15. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
$2,340 nightly
The price is $2,673
Sep 28 - Sep 29
Total with taxes and fees
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

16. 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
$192 nightly
The price is $219
Oct 8 - Oct 9
Total with taxes and fees
Driftwood Resort
A modern living room with a blue sofa, a wooden coffee table, and a kitchen area with cabinets and a countertop.

17. Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this property! Very clean, just steps to the beach and close to everything we love in the Hamptons!"
United States
Pamela
$502 nightly
The price is $571
Sep 27 - Sep 28
Total with taxes and fees
Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

18. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$469 nightly
The price is $536
Sep 27 - Sep 28
Total with taxes and fees
Charming Accommodations in the Hamptons
A campground with several tents and trees, a grassy area, and a view of the water.

19. Safari Tent Glamping,S3-CedarPt, East Hampton, NY

Safari Tent Glamping,S3-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"The store was great and the upgrades were perfect. The pizza was excellent and hope to be back soon"
United States
Joseph
$260 nightly
The price is $298
Sep 25 - Sep 26
Total with taxes and fees
Safari Tent Glamping,S3-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

Zey Hotel

Zey Hotel

10/10 Excellent
"Lovely hotel, great location and lovely courtyard!"
Martina 1-night trip
Posted 7 hours ago
Zey Hotel

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 $146 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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Wainscott is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

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.