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Wainscott Woods Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Wainscott Woods vacation rentals

A driveway with a parked car, surrounded by trees and illuminated pathway lights.

1. 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.
The price is ￥45,252
￥93,243 total
includes taxes & fees
Sep 29 - Sep 30
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (290 reviews)
"Great place!"
United States
Christine
The price is ￥46,343
￥67,102 total
includes taxes & fees
Sep 27 - Sep 28
Cliffside Resort Condominiums
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

3. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is ￥39,251
￥85,846 total
includes taxes & fees
Sep 9 - Sep 10
Charming Accommodations in the Hamptons
A modern house with a deck, outdoor seating, and a fire pit.

4. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (52 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is ￥47,615
￥54,400 total
includes taxes & fees
Sep 13 - Sep 14
North Fork Resort

5. 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
The price is ￥24,698
￥32,535 total
includes taxes & fees
Oct 4 - Oct 5
Windward Shores Ocean Resort

6. 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
The price is ￥26,510
￥35,460 total
includes taxes & fees
Sep 21 - Sep 22
Driftwood Resort
A row of tents with a grassy field and trees in the background.

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.
The price is ￥34,125
￥51,689 total
includes taxes & fees
Sep 7 - Sep 8
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
A row of tents with a grassy field and trees in the background.

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

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is ￥34,125
￥51,689 total
includes taxes & fees
Sep 7 - Sep 8
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
A spacious hallway with high ceilings, arched columns, and chandeliers.

9. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,398 reviews)
"Beautiful property"
United States
John
The price is ￥39,298
￥48,007 total
includes taxes & fees
Sep 10 - Sep 11
Montauk Manor
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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.
The price is ￥107,867
￥200,153 total
includes taxes & fees
Sep 7 - Sep 8
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A covered patio with a table and chairs, large windows, and a view of greenery.

11. 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
The price is ￥56,074
￥94,084 total
includes taxes & fees
Sep 7 - Sep 8
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A small cabin with a porch, surrounded by trees and a fenced area.

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.
The price is ￥46,840
￥97,415 total
includes taxes & fees
Sep 14 - Sep 15
Lovely studio with AC in charming Sag Harbor
A spacious room with a wooden dining table, white chairs, and a large window providing a view of the outdoors.

13. Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool

Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool
East Hampton North
The price is ￥102,889
￥229,662 total
includes taxes & fees
Sep 28 - Sep 29
Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool
A modern living room with a fireplace, a sofa, a chair, and a coffee table.

14. Beautiful East Hampton Retreat

Beautiful East Hampton Retreat
East Hampton
9.6 out of 10, Exceptional, (5 reviews)
"The host was very easy to work with. He was attentive and responsive. The home was exactly as advertised and was clean and nice to stay in!"
United States
Jonathan S.
Beautiful East Hampton Retreat
A dining area with a round table, six chairs, and a chandelier.

15. 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.
The price is ￥67,958
￥272,964 total
includes taxes & fees
Sep 9 - Sep 10
BlackBerry Private home with jacuzzi yearlong

16. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (448 reviews)
"It was wonderful"
United States
christopher
The price is ￥22,507
￥27,442 total
includes taxes & fees
Sep 28 - Sep 29
Montauk Oceanside Suites
A wooden pathway leading to a beach with scattered rocks and greenery.

17. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥30,962
￥66,394 total
includes taxes & fees
Sep 7 - Sep 8
Beach Block Hideaway
A beach with people relaxing on chairs and sunbathing.

18. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is ￥27,866
￥57,232 total
includes taxes & fees
Sep 13 - Sep 14
Harbor Heights
A campsite with several tents and a picnic table.

19. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (5 reviews)
"It was a really great experience! We barbecued and made a camp fire. Took a walk on the beach. Played in the playground. The pizza and breakfast sandwiches in the café were delicious! We will definitely be coming back!"
United States
Brian F.
The price is ￥34,125
￥53,684 total
includes taxes & fees
Sep 7 - Sep 8
Safari Tent Glamping,D28-CedarPt, East Hampton, NY
A campground with several tents and trees, a grassy area, and a view of the water.

20. 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.
The price is ￥34,125
￥53,684 total
includes taxes & fees
Sep 7 - Sep 8
Safari Tent Glamping,D27-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 Woods Hotel Reviews

Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Loved our stay! The staff was very helpful. Would definitely stay again!"
Diane 1-night trip
Posted 6 hours ago
Hampton's Vacation Inn

Find out more about Wainscott Woods

Search for holiday rentals in Wainscott Woods on Expedia! You can easily find your home rentals, villas, holiday apartments in Wainscott Woods using one of the methods below:

  • View our selection of featured holiday rentals in Wainscott Woods
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Look no further and take a look at our great range of rental properties in Wainscott Woods!

Frequently asked questions

Can I find a vacation rental in Wainscott Woods?

Yes, we have vacation rentals near the most popular attractions in Wainscott Woods, or you can go with a secluded option if you want a relaxing place to stay.

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

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental near Wainscott Woods 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 Woods?

With 18 Expedia vacation rentals, you're sure to find just the right place for your Wainscott Woods stay.

What’s there to see and do in Wainscott Woods?

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 Georgica Beach. Wolffer Estates Vineyard and The Jewish Center of the Hamptons are a couple of places you'll find in the larger area.

What’s a vacation rental in Wainscott Woods like?

A vacation rental is a private property you can stay in for a couple of days or more in Wainscott Woods. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.