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Sep 16 - Sep 17
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Sep 17 - Sep 18
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Sep 18 - Sep 20
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Sep 25 - Sep 27

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Our top choices for Wainscott Woods hotels

Two people sitting by a poolside with a dining setup including plates, a bottle, and a wine glass.
A compact kitchenette with a fridge, a sink, and a coffee maker.
A well-maintained garden with a wooden cabin, a small tree, and a paved pathway.
A patio with four wicker chairs and a table, a blue umbrella, and a wooden building in the background.

1. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
United States
Ivan
￥114,730
￥136,509 total
includes taxes & fees
Sep 17 - Sep 18
Wainscott Woods Retreat
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.
A wooden building with a white window and a balcony.
A beach with pebbles and sand, a sunset, and a calm sea.
A room with a large bay window, a chandelier, and wall sconces.

2. The Sagaponack

The Sagaponack
Wainscott
United States
Jane
￥38,741
￥50,430 total
includes taxes & fees
Oct 6 - Oct 7
The Sagaponack
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

3. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
￥49,977
￥57,100 total
includes taxes & fees
Oct 6 - Oct 7
Sag Harbor Inn
An outdoor dining area with trees and tables under string lights.
A garden pathway leading to a white picket fence and a building with an American flag.
A living room with a fireplace, a television mounted above it, and a dining area in the background.
A white house with a sign reading "The 1770 House Restaurant & Inn."

4. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
￥75,390
￥103,063 total
includes taxes & fees
Sep 21 - Sep 22
The 1770 House Restaurant & Inn
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bathtub surrounded by candles and flower petals.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

5. A Room At The Beach

A Room At The Beach
Bridgehampton
United States
Barbara
￥45,673
￥52,181 total
includes taxes & fees
Oct 4 - Oct 5
A Room At The Beach
A beach chair with a striped cushion and a bag with a floral design.
A person riding a bicycle with a basket on a road.
A two-story white house with a brick pathway leading to the front door, surrounded by a white picket fence and a flag.
A room with a bookshelf, a chair, a lamp, and a wall mural depicting a beach scene.

6. The Hedges Inn

The Hedges Inn
East Hampton
United States
Lauren
￥69,274
￥88,245 total
includes taxes & fees
Sep 29 - Sep 30
The Hedges Inn
A beach with a lifeguard tower, sandy dunes, and the ocean.
A large white building with green shutters, surrounded by lush greenery and hydrangea flowers.
A breakfast buffet table with various pastries and fruits, set against a backdrop of large windows overlooking a garden.
A large, white building with a green awning, surrounded by well-maintained lawns and colorful flower beds.

7. The Huntting Inn

The Huntting Inn
Egypt Lane Historic District
Canada
Josie
￥69,081
￥80,475 total
includes taxes & fees
Oct 4 - Oct 5
The Huntting Inn
A dining area with a fireplace, bookshelves, and a view of the bar area.
A two-story building with a brick pathway leading to the entrance.
A room with two armchairs, a small table with a vase of flowers, and a patterned rug.
A bedroom with a wooden headboard, a bedside table with a lamp, and a bed with a grey blanket.

8. Bridgehampton Inn

Bridgehampton Inn
Bridgehampton
United States
Leslie
￥46,121
￥52,694 total
includes taxes & fees
Oct 6 - Oct 7
Bridgehampton Inn

9. East Hampton House Resort

East Hampton House Resort
East Hampton North
Canada
Suzette
￥38,395
￥48,084 total
includes taxes & fees
Sep 28 - Sep 29
East Hampton House Resort
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A living room with a fireplace, two sofas, a coffee table, and a chair.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

10. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
￥42,854
￥53,858 total
includes taxes & fees
Oct 12 - Oct 13
Journey East Hampton
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A modern hotel room with a bed, bedside table, and a view of the garden.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A large, white, two-story building with a covered porch and a bicycle parked in front.

11. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
￥145,933
￥167,268 total
includes taxes & fees
Sep 21 - Sep 22
Topping Rose House
A two-story building with a porch and a flagpole.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
A hotel interior with a long corridor, seating areas, and a reception desk.

12. The Maidstone

The Maidstone
East Hampton
United States
Steven
￥42,428
￥50,899 total
includes taxes & fees
Oct 13 - Oct 14
The Maidstone
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A spacious living room with a fireplace, comfortable seating, and large windows.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

13. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
￥68,719
￥86,363 total
includes taxes & fees
Oct 6 - Oct 7
Faraway Sag Harbor
A house with a sloped roof, large windows, and a pathway leading to the entrance.
A wooden gate leading to a pathway surrounded by lush greenery and trees.
A cozy living room with a white sofa, a dining table with chairs, a chandelier, a potted plant, and framed pictures on the wall.
A dining area with a chandelier, a large table, chairs, and a vase with flowers.

14. Mill House Inn

Mill House Inn
Pantigo Road Historic District
Canada
Ronald
￥134,969
￥195,067 total
includes taxes & fees
Sep 21 - Sep 22
Mill House Inn
A two-story house with a steeply pitched roof, green shutters, and a brick entrance.
A living room with a fireplace, a white armchair, a glass coffee table with flowers, and a bookshelf.
A cozy living room with a wooden table, a red sofa, and a balcony with a view of trees and a body of water.
A swimming pool with lounge chairs and a white fence.

15. Head of Pond House

Head of Pond House
Water Mill
United States
Liz
￥100,525
￥114,850 total
includes taxes & fees
Sep 24 - Sep 25
Head of Pond House
A beach with waves gently lapping onto the shore.
A patio with four wicker chairs arranged around a round table with a fire pit in the center, set in a grassy outdoor area with trees and a fence in the background.
A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.

16. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
￥107,093
￥128,471 total
includes taxes & fees
Oct 6 - Oct 7
The Roundtree, Amagansett
A deck with outdoor seating, overlooking a body of water with a sunset view.
A restaurant with green booths, wooden chairs, and round tables.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

17. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Morris
￥78,644
￥98,836 total
includes taxes & fees
Sep 17 - Sep 18
The Pridwin Hotel
A staircase with a white railing, a white chandelier, and framed artwork on the walls.
A wooden bed with white and red pillows, a blue throw, and a nightstand with drawers.
A covered outdoor seating area with white canopies and brown furniture.
Two wine bottles with labels on a counter.

18. Harpoon House

Harpoon House
Southampton
United States
Kim
￥37,812
￥43,201 total
includes taxes & fees
Oct 1 - Oct 2
Harpoon House
A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.
A kitchen counter with a coffee maker, thermos, fruits, and breakfast items.
A hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.

19. The Atlantic Hotel

The Atlantic Hotel
Southampton
United States
Jessa
￥18,499
￥25,012 total
includes taxes & fees
Oct 1 - Oct 2
The Atlantic Hotel
A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace in the background.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A beach scene with a sunset, calm sea, and a few people fishing.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

20. Hamlet Inn

Hamlet Inn
Southampton
United States
Thomas
￥19,663
￥25,415 total
includes taxes & fees
Sep 27 - Sep 28
Hamlet Inn
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Learn more about Wainscott Woods

Check out Wolffer Estates Vineyard and Georgica Beach—just a couple of the sights around Wainscott Woods.

See all hotels in Wainscott Woods
Brioche buns with chocolate chips priced at $3.50.
Photo by Miriam Marcus

Top Wainscott Woods Hotel Reviews

Montauk Manor

Montauk Manor

10/10 Excellent
"We loved the room and views. Will definitely come back."
miwha 2-night trip
Posted 2 hours ago
Montauk Manor
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"The view is the best! Beach is beautiful. Rooms are clean however the rooms need some maintenance done. Holes in doors and curtain rods almost falling down . Air conditioning units need to be replaced. Fans on high all the time and turn on and off every 10 min. Had to turn off at night . The staff are very helpful and courteous. We will return again"
michelle 1-night trip
Posted 15 hours ago
Ocean Surf Resort
Marram

Marram

10/10 Excellent
"Amazing hip on the beach Cool best food anywhere"
Peter 1-night trip
Posted 16 hours ago
Marram
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room clean was especially helpful. Parking spaces were wide with ample space to unload and open passenger doors."
barbara 5-night trip
Posted 19 hours ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."
Joseph 3-night trip
Posted 2 days ago
Sound View Greenport
Sun N Sound

Sun N Sound

8/10 Good
"Very nice and clean. Pool was excellent. Only complaint was that the bathroom sink and shower drains were slow to drain. I'll give it a 8/10"
Kathy 2-night trip
Posted 2 days ago
Sun N Sound
North Fork Resort

North Fork Resort

10/10 Excellent
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
Harold 1-night trip
Posted 2 days ago
North Fork Resort
Zey Hotel

Zey Hotel

10/10 Excellent
"My Husband Phil & I had the Best Stay. Very Quaint Hotel, just a couple of blocks from waterfront.Absolutely spotless, so many sitting areas, Coffee, tea water and ice available 24-7. Our room was spotless, decorated so well. We also had a balcony. James and all staff were so Pleasant and so accommodating. Can't wait to return for another stay. Thank you James .. Phil & Jenn"
Jennifer 1-night trip
Posted 2 days ago
Zey Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Absolutely gorgeous stay!"
Sabrina 1-night trip
Posted 3 days ago
Gurney's Montauk Resort & Seawater Spa

More cheap stays in Wainscott Woods

Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
￥16,675
￥19,813 total
Oct 8 - Oct 9
includes taxes & fees
8.4/10 Very Good! (961 reviews)
Kenny's Tipperary Inn
Hampton's Vacation Inn

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY
￥19,088
￥21,807 total
Sep 17 - Sep 18
includes taxes & fees
Hampton's Vacation Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
￥18,499
￥25,012 total
Oct 1 - Oct 2
includes taxes & fees
7.2/10 Good! (1,007 reviews)
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
￥19,622
￥29,166 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (316 reviews)
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
￥22,283
￥33,007 total
Sep 29 - Sep 30
includes taxes & fees
Montauk Blue Hotel
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
￥32,810
￥37,485 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (782 reviews)
The Hampton Maid

Frequently asked questions

What's the best place for a stay in Wainscott Woods?
Located 14.3 mi (22.9 km) from the heart of Wainscott Woods, Gurney's Montauk Resort & Seawater Spa is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Sound View Greenport and The Atlantic Hotel. See all available top hotels, or vacation rentals in Wainscott Woods.
What's the top vacation rental that Wainscott Woods has to offer?
Unobstructed Ocean Views ! A Beautiful Montauk Getaway: Visitors like this Wainscott Woods vacation home rental. It 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. See all vacation rentals in Wainscott Woods.
If I need to cancel my hotel reservation in Wainscott Woods, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Wainscott Woods.
Where can I learn more about changing or cancelling my trip to Wainscott Woods?
For additional details about picking new dates or cancelling your trip to Wainscott Woods, go to https://www.expedia.com/service/.
What's the best pet-friendly place to stay in Wainscott Woods?
380 Inn is a top hotel for people traveling with their pets, and offers free newspapers and in-room kitchenettes for its human guests. See more pet-friendly hotel accommodations in Wainscott Woods.
What are some hotels with pools in Wainscott Woods?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport and The Atlantic Hotel are a couple of other choices that feature an onsite pool. View all hotels with pools in Wainscott Woods.
What's it like staying in Wainscott Woods?
Visitors to Wainscott Woods are sure to find plenty to explore and enjoy. In Wainscott Woods, there are 22 hotels and other accommodations to choose from. Find out more about Wainscott Woods.
What should I see while I'm in Wainscott Woods?
Places to visit in the wider area include Wolffer Estates Vineyard, Georgica Beach, and The Jewish Center of the Hamptons. You'll also find East Hampton Main Beach and Guild Hall in the area. Check out what more to see and do in Expedia's Wainscott Woods guide.
What's the weather like in Wainscott Woods?
The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Wainscott Woods is 57 inches.

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