Wainscott Woods Holiday Rentals, Wainscott: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Wainscott Woods

Family friendly

Apartment

Condo

Hot tub

Pet friendly

Spa

Pool

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

1. Wainscott Woods Retreat

Wainscott

Ivan

Rp11.498.112

Rp13.757.633 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 wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.

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

A wooden building with a white window and a balcony.

2. The Sagaponack

Wainscott

Jane

Rp4.508.605

Rp6.039.230 total

includes taxes & fees

4 Oct - 5 Oct

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

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

3. The 1770 House Restaurant & Inn

East Hampton

Lisa

Rp8.672.380

Rp11.855.654 total

includes taxes & fees

21 Sept - 22 Sept

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

A hotel lobby with a sofa, chairs, tables, and a large window.

4. Sag Harbor Inn

Sag Harbor

Loretta

Rp5.755.212

Rp6.575.330 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 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 bar area with shelves stocked with various bottles and glasses.

5. Topping Rose House

Bridgehampton

Adam

Rp17.486.712

Rp20.040.673 total

includes taxes & fees

10 Sept - 11 Sept

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 bedroom with a wooden headboard, a bedside table with a lamp, and a bed with a grey blanket.

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

6. Bridgehampton Inn

Bridgehampton

Leslie

Rp5.311.137

Rp6.068.018 total

includes taxes & fees

1 Oct - 2 Oct

7. East Hampton House Resort

East Hampton North

Suzette

Rp4.396.343

Rp5.505.819 total

includes taxes & fees

28 Sept - 29 Sept

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

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

8. The Huntting Inn

Egypt Lane Historic District

James Patrick

Rp7.910.042

Rp9.214.734 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

A modern living room with a stone wall, a flat-screen TV mounted above a door, a dark sofa, and a glass coffee table with a vase of flowers.

A bedroom with a large bed, a chandelier, and multiple windows.

A beach with sand and sparse vegetation.

9. The Hampton Maid

Hampton Bays

SABINA

Rp4.631.184

Rp5.291.129 total

includes taxes & fees

8 Sept - 9 Sept

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

A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

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.

10. Journey East Hampton

East Hampton North

NAKUL

Rp5.510.971

Rp6.925.794 total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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.

11. The Bentley Hotel Southampton

Southampton

Frank

Rp2.565.014

Rp3.374.604 total

includes taxes & fees

27 Sept - 28 Sept

A beach with waves gently lapping onto the shore.

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

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

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.

12. The Roundtree, Amagansett

Amagansett North

Ryan

Rp12.332.446

Rp14.794.299 total

includes taxes & fees

1 Oct - 2 Oct

A bedroom with a bed, bedside table, lamp, and a view of the outdoors through a window.

A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.

A covered patio area with outdoor seating, a potted plant, and a well-maintained lawn.

A living room area with a sofa, a dining table, and a separate queen bedroom.

13. Southampton Long Island Hotel

Southampton

William

Rp3.531.056

Rp4.211.006 total

includes taxes & fees

16 Sept - 17 Sept

A snow-covered pathway leading to a building with a porch.

A well-maintained garden with a central pathway leading to a house.

14. Southampton Inn

Southampton

Kevin

Rp3.996.675

Rp4.855.516 total

includes taxes & fees

4 Oct - 5 Oct

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

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

15. The Harbor Front Inn

Greenport

Michael

Rp4.620.156

Rp5.785.839 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel room with a large bed, a framed picture on the wall, and a wooden floor.

A spacious room with wooden flooring, a bar area with stools, and large windows allowing natural light.

A two-story building with a sign reading "Squiretown Rd" and a storefront with a sign that says "B&B."

A compact kitchen with white cabinetry, a built-in dishwasher, and a coffee maker on the countertop.

16. Hampton Bays Hotel on Main

Hampton Bays

Deborah

Rp2.095.857

Rp2.394.517 total

includes taxes & fees

8 Sept - 9 Sept

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 modern living room with a sofa, a dining table with chairs, a TV on a wooden stand, and a large window with a view of trees.

17. Head of Pond House

Water Mill

Liz

Rp33.216.768

Rp37.950.158 total

includes taxes & fees

9 Sept - 10 Sept

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 house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

A beach scene with a sunset, calm sea, and a few people fishing.

18. Hamlet Inn

Southampton

Thomas

Rp2.251.460

Rp2.910.112 total

includes taxes & fees

27 Sept - 28 Sept

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

A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

A bathtub surrounded by candles and flower petals.

19. 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

Rp5.844.027

Rp6.676.756 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.

A hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.

20. The Atlantic Hotel

Southampton

Jessa

Rp2.118.237

Rp2.864.162 total

includes taxes & fees

1 Oct - 2 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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