Hotels in Wainscott Woods from P8,604 for 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 well-maintained garden with a wooden cabin, a small tree, and a paved pathway.

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

A compact kitchenette with a fridge, a sink, and a coffee maker.

1. Wainscott Woods Retreat

Wainscott

Ivan

P40,433

P48,379 total

includes taxes & fees

Sep 10 - Sep 11

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 wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.

2. The Sagaponack

Wainscott

Jane

P15,878

P21,268 total

includes taxes & fees

Oct 4 - Oct 5

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

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

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

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

3. Sag Harbor Inn

Sag Harbor

Loretta

P18,775

P21,451 total

includes taxes & fees

Sep 24 - Sep 25

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 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.

4. Topping Rose House

Bridgehampton

Adam

P61,649

P70,653 total

includes taxes & fees

Sep 13 - Sep 14

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.

5. 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

P20,581

P23,514 total

includes taxes & fees

Oct 4 - Oct 5

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

A living room with a fireplace, a television mounted above it, and a dining area in the background.

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.

6. The 1770 House Restaurant & Inn

East Hampton

Lisa

P30,497

P41,691 total

includes taxes & fees

Sep 21 - Sep 22

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.

7. The Hedges Inn

East Hampton

Lauren

P33,638

P42,113 total

includes taxes & fees

Sep 15 - Sep 16

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

A large, white building with a green awning, surrounded by well-maintained lawns and colorful flower beds.

A breakfast buffet table with various pastries and fruits, set against a backdrop of large windows overlooking a garden.

A large white building with green shutters, surrounded by lush greenery and hydrangea flowers.

8. The Huntting Inn

Egypt Lane Historic District

James Patrick

P27,857

P32,452 total

includes taxes & fees

Oct 4 - Oct 5

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 white house with a red door, surrounded by a well-maintained garden with hedges and a stone pathway.

9. The Maidstone

East Hampton

Steven

P24,483

P29,371 total

includes taxes & fees

Sep 10 - Sep 11

A two-story house with a steeply pitched roof, green shutters, and a brick entrance.

A swimming pool with lounge chairs and a white fence.

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 living room with a fireplace, a white armchair, a glass coffee table with flowers, and a bookshelf.

10. Head of Pond House

Water Mill

Liz

P116,807

P133,452 total

includes taxes & fees

Sep 9 - Sep 10

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

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

11. Mill House Inn

Pantigo Road Historic District

Ronald

P54,597

P78,908 total

includes taxes & fees

Sep 8 - Sep 9

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.

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

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

12. Bridgehampton Inn

Bridgehampton

Leslie

P18,704

P21,370 total

includes taxes & fees

Oct 1 - Oct 2

A pool area with umbrellas, potted plants, and a pathway leading to a building.

A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

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

A spacious living room with a fireplace, comfortable seating, and large windows.

13. Faraway Sag Harbor

Sag Harbor

Joseph

P34,062

P42,807 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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.

14. Journey East Hampton

East Hampton North

NAKUL

P19,408

P24,391 total

includes taxes & fees

Oct 4 - Oct 5

15. East Hampton House Resort

East Hampton North

Suzette

P15,443

P19,341 total

includes taxes & fees

Sep 28 - Sep 29

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

Two wine bottles with labels on a counter.

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.

16. Harpoon House

Southampton

Kim

P15,013

P17,153 total

includes taxes & fees

Sep 7 - Sep 8

A brick house with a covered porch, a chimney, and a well-maintained lawn.

A spacious living room with a staircase, a fireplace, and a coffee table with books and flowers.

A modern kitchen with a marble countertop, a coffee maker, and a fruit tray.

A small brick house with a chimney, surrounded by a well-maintained lawn and trees.

17. The Reform Club

Amagansett North

Cathleen

P87,746

P108,269 total

includes taxes & fees

Sep 22 - Sep 23

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 house with a gravel driveway, a child holding an adult's hand, and a lamp post.

18. The Roundtree, Amagansett

Amagansett North

Ryan

P43,431

P52,101 total

includes taxes & fees

Oct 1 - Oct 2

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.

19. The Pridwin Hotel

Shelter Island Heights

Anna

P33,423

P42,004 total

includes taxes & fees

Sep 14 - Sep 15

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 modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

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.

20. The Bentley Hotel Southampton

Southampton

Frank

P9,033

P11,884 total

includes taxes & fees

Sep 27 - Sep 28

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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."

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!"

The Shoals Suites and Slips

10/10 Excellent

"Loved everything about our stay!"

More cheap stays in Wainscott Woods