𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Wainscott Woods from RM556 (2026) - Fully Refundable Options

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Go beyond your typical stay in Wainscott Woods

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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 hotel room with two beds, a kitchenette, a refrigerator, and a wall-mounted shelf with bottles.

A patio with four wicker chairs and a table, a blue umbrella, and a wooden building in the background.

1. Wainscott Woods Retreat

Wainscott

Ivan

RM2,617

RM3,132 total

includes taxes & fees

10 Sept - 11 Sept

Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

A beach with pebbles and sand, a sunset, and a calm sea.

A wooden building with a white window and a balcony.

A room with a large bay window, a chandelier, and wall sconces.

2. The Sagaponack

Wainscott

Jane

RM1,027

RM1,375 total

includes taxes & fees

4 Oct - 5 Oct

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

A bathtub surrounded by candles and flower petals.

A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

3. A Room At The Beach

Bridgehampton

"I absolutely loved my stay at **A Room at the Beach** in Bridgehampton. Every detail of the property feels thoughtfully designed, creating an atmosphere that is both elegant and incredibly relaxing. The rooms are stylish, comfortable, and well appointed. They strike the perfect balance between luxury and warmth. What really sets this property apart, though, are the charming grounds. They've created gathering spaces that invite you to pause, read, enjoy a morning coffee, and take in the...

Barbara

RM1,331

RM1,521 total

includes taxes & fees

4 Oct - 5 Oct

A waterfront property with a large house, multiple boats docked, and lush greenery.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

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.

4. Sag Harbor Inn

Sag Harbor

Loretta

RM1,311

RM1,498 total

includes taxes & fees

4 Oct - 5 Oct

A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

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 bar area with shelves stocked with various bottles and glasses.

A large, white, two-story building with a covered porch and a bicycle parked in front.

5. Topping Rose House

Bridgehampton

Adam

RM3,980

RM4,562 total

includes taxes & fees

7 Sept - 8 Sept

A two-story house with a front porch, columns, and a well-lit entrance.

A bathroom with two white robes hanging on a wooden rack, a window with a white blind, and a wooden towel rack with towels.

A garden statue of a seated figure with two potted plants on either side.

A modern kitchen with a central island, bar stools, pendant lighting, and a view into the dining area.

6. The Maidstone

East Hampton

Steven

RM1,977

RM2,372 total

includes taxes & fees

16 Sept - 17 Sept

An outdoor dining area with trees and tables under string lights.

A white house with a sign reading "The 1770 House Restaurant & Inn."

A restaurant with wooden beams, tables with white tablecloths, and a bar area.

A garden pathway leading to a white picket fence and a building with an American flag.

7. The 1770 House Restaurant & Inn

East Hampton

Lisa

RM1,977

RM2,703 total

includes taxes & fees

21 Sept - 22 Sept

A dining area with a fireplace, bookshelves, and a view of the bar area.

A room with two armchairs, a small table with a vase of flowers, and a patterned rug.

An outdoor wedding setup with white chairs, a table with floral arrangements, and a white canopy.

A two-story building with a brick pathway leading to the entrance.

8. Bridgehampton Inn

Bridgehampton

Leslie

RM1,210

RM1,382 total

includes taxes & fees

1 Oct - 2 Oct

A beach with a lifeguard tower, sandy dunes, and the ocean.

A bar area with wooden bar stools, a television screen, and shelves of bottles and glasses.

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.

9. The Huntting Inn

Egypt Lane Historic District

James Patrick

RM1,802

RM2,099 total

includes taxes & fees

4 Oct - 5 Oct

A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

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

East Hampton North

NAKUL

RM1,255

RM1,577 total

includes taxes & fees

4 Oct - 5 Oct

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 hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

11. Faraway Sag Harbor

Sag Harbor

Joseph

RM2,203

RM2,768 total

includes taxes & fees

7 Sept - 8 Sept

12. East Hampton House Resort

East Hampton North

Suzette

RM1,001

RM1,254 total

includes taxes & fees

28 Sept - 29 Sept

A beach chair with a striped cushion and a bag with a floral design.

A dining area with a table set for two, wicker chairs, a painting of sailboats, and a wooden ceiling with a grid pattern.

A two-story white house with a brick pathway leading to the front door, surrounded by a white picket fence and a flag.

A person riding a bicycle with a basket on a road.

13. The Hedges Inn

East Hampton

Lauren

RM2,181

RM2,730 total

includes taxes & fees

13 Sept - 14 Sept

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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

14. The Pridwin Hotel

Shelter Island Heights

Anna

RM2,154

RM2,707 total

includes taxes & fees

7 Sept - 8 Sept

A house with a sloped roof, large windows, and a pathway leading to the entrance.

A dining area with a chandelier, a large table, chairs, and a vase with flowers.

A wooden gate leading to a pathway surrounded by lush greenery and trees.

A covered porch with white railings, green cushioned chairs, hanging flower baskets, and pendant lights.

15. Mill House Inn

Pantigo Road Historic District

Ronald

RM3,534

RM5,108 total

includes taxes & fees

15 Sept - 16 Sept

A staircase with a white railing, a white chandelier, and framed artwork on the walls.

A covered outdoor seating area with white canopies and brown furniture.

A wooden bed with white and red pillows, a blue throw, and a nightstand with drawers.

Two wine bottles with labels on a counter.

16. Harpoon House

Southampton

Kim

RM971

RM1,109 total

includes taxes & fees

7 Sept - 8 Sept

A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

17. The Bentley Hotel Southampton

Southampton

Frank

RM584

RM769 total

includes taxes & fees

27 Sept - 28 Sept

A beach with waves gently lapping onto the shore.

A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."

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 modern bedroom with a bed, a desk with a chair, a television, and a large mirror.

18. The Roundtree, Amagansett

Amagansett North

Ryan

RM2,809

RM3,369 total

includes taxes & fees

1 Oct - 2 Oct

A waterfront restaurant with wooden tables and white chairs, set against a backdrop of a marina and calm water.

A spacious interior with a wooden staircase, a blue sofa, and a white chair.

A spacious lobby with a large seating area, a staircase, and a view of the upper floor.

A modern kitchen with a wooden countertop, a black sink, and a pendant light.

19. EHP Resort & Marina

East Hampton

theresa

RM2,326

RM2,923 total

includes taxes & fees

1 Oct - 2 Oct

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A storefront with a sign reading "THE SHOALS".

20. The Shoals Suites and Slips

Southold

Melissa

RM816

RM1,034 total

includes taxes & fees

1 Oct - 2 Oct

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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.

Top Wainscott Woods Hotel Reviews

Hampton's Vacation Inn

10/10 Excellent

"Loved our stay! The staff was very helpful. Would definitely stay again!"

The Hampton Maid

10/10 Excellent

"wonderful hotel."

Ocean Surf Resort

10/10 Excellent

"Stutaff was kind and the room was clean. It was very nice to be close to the sea. I had a good time. Thank you"

Zey Hotel

10/10 Excellent

"Great location, and James is there for your every need! Not posh, but great value and a friendly staff make for a great experience in Greenport!"

Kenny's Tipperary Inn

8/10 Good

"Nice hotel and very clean, and the staff were very courteous and helpful. Beach is walking distance right down the road. Perfect location if you're looking for something by the beach."

Faraway Sag Harbor

8/10 Good

"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Great beachfront property! Spa is amazing!"

Montauk Yacht Club

10/10 Excellent

"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property."

The Bentley Hotel Southampton

10/10 Excellent

"A well thought out space. Staff is welcoming and helpful. The Room met our expectations. They even offer a beach pass for the Southampton town beach!"

More cheap stays in Wainscott Woods