Wainscott Holiday Rentals, New York: Private House Rentals

A coastal landscape with a beach, ocean waves, and a sunset sky.

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Our top choices for Wainscott hotels

A hotel room with a bed, two bedside tables, a lamp, a chair, and a dresser.

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 wooden building with a white window and a balcony.

1. The Sagaponack

Wainscott

Jane

5.201.860 ₫

6.979.440 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

A bar area with shelves stocked with various bottles and glasses.

2. Topping Rose House

Bridgehampton

16.210.458 ₫

18.611.154 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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 room with a bookshelf, a chair, a lamp, and a wall mural depicting a beach scene.

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

3. The Hedges Inn

East Hampton

Lauren

9.306.436 ₫

12.161.602 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A spacious bedroom with a large bed, a sitting area with a sofa, a chair, and a small ottoman. There are two windows with curtains, a fireplace, and a flat-screen TV mounted on the wall.

A kitchen with a central island, two wicker chairs, and a bar area with glasses.

A living room with a sofa, a small table, a vintage refrigerator, and a large window with curtains.

A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.

4. The Maidstone

East Hampton

Steven

6.388.294 ₫

7.663.782 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A bathtub surrounded by candles and flower petals.

5. A Room At The Beach

Bridgehampton

Samantha

7.673.728 ₫

8.767.124 ₫ total

includes taxes & fees

22 Oct - 23 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 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.

6. The Huntting Inn

Egypt Lane Historic District

Josie

9.925.569 ₫

11.599.483 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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.

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.

7. Bridgehampton Inn

Bridgehampton

Leslie

7.748.884 ₫

8.853.165 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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 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.

8. Sag Harbor Inn

Sag Harbor

Terri

5.675.604 ₫

6.484.376 ₫ total

includes taxes & fees

9 Nov - 10 Nov

9. East Hampton House Resort

East Hampton North

Tina

4.112.610 ₫

5.403.486 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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

10. The 1770 House Restaurant & Inn

East Hampton

Lisa

10.431.190 ₫

14.260.279 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 living room with a fireplace, two sofas, a coffee table, and a chair.

11. Journey East Hampton

East Hampton North

Erika

6.414.210 ₫

8.061.140 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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

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.

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

12. Mill House Inn

Pantigo Road Historic District

Rhett

8.422.700 ₫

12.173.263 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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

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

A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

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

13. Faraway Sag Harbor

Sag Harbor

Thomas

9.796.248 ₫

12.311.523 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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 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.

14. The Roundtree, Amagansett

Amagansett North

Dwight

15.403.829 ₫

18.478.722 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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

A two-story house with a covered patio and a small garden area.

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

15. The Reform Club

Amagansett North

20.263.072 ₫

25.002.518 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

16. Southampton Inn

Southampton

Kevin

5.183.200 ₫

6.343.978 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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

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

A spacious bar area with a large floral arrangement, seating with cushioned chairs, and a view of the upper level through large windows.

17. EHP Resort & Marina

East Hampton

theresa

6.908.946 ₫

8.682.637 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A spacious room with wicker furniture, large windows, and a view of the sea.

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

A beach bar with wooden chairs and a small table, overlooking the sea.

A coastal building with large windows, a deck, and a view of the sea at sunset.

18. Sound View Greenport

Greenport

4.968.875 ₫

6.417.102 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

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

A bar area with wooden bar stools and a bookshelf.

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

19. The Harbor Front Inn

Greenport

Antrii

4.638.964 ₫

6.040.178 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A lakeside patio with outdoor seating and a view of the water.

A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

20. Silver Sands Motel & Beach Bungalows

Greenport

Keith

7.260.960 ₫

8.295.647 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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Learn more about Wainscott

Tucked between East Hampton and Bridgehampton, this Hamptons hamlet offers pristine beaches with gentle waves perfect for families. Rent bikes to explore Wainscott's farm stands selling local produce, then visit nearby Sag Harbour for boutique shopping and waterfront dining.

See all hotels in Wainscott

Top Wainscott Hotel Reviews

Zey Hotel

10/10 Excellent

"It worked out well for me."

Offshore Montauk

10/10 Excellent

"This was my first time staying @ this property. The staff were so kind & helpful! The gentleman at the front desk was beyond helpful from the moment we checked in, to the moment we left! This team knows the meaning of hospitality! 5 star service Would stay here again !! Thank you :)"

Montauk Blue Hotel

10/10 Excellent

"Loved the ocean front and pool. Easy walk to town’s"

Sound View Greenport

10/10 Excellent

"The breakfast could have had a better choice."

The Bentley Hotel Southampton

10/10 Excellent

"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."

Ocean Vista Resort

10/10 Excellent

"Ocean Vista was a very well-maintained property. Staff was very welcoming and pleasant as well as professional. Enjoyed our stay we’ll go back."

Ocean Surf Resort

10/10 Excellent

"Perfect for weekend stay"

More cheap stays in Wainscott

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY

2.785.711 ₫

3.309.992 ₫ total

5 Nov - 6 Nov

includes taxes & fees

8.4/10 Very good! (983 reviews)

The Atlantic Hotel

1655 County Road 39 Southampton NY

2.777.317 ₫

3.821.385 ₫ total

28 Oct - 29 Oct

includes taxes & fees

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

3.706.266 ₫

4.234.408 ₫ total

10 Nov - 11 Nov

includes taxes & fees

9.6/10 Exceptional! (600 reviews)

Ocean Surf Resort

84 South Emerson Avenue Montauk NY

2.824.844 ₫

4.354.730 ₫ total

27 Oct - 28 Oct

includes taxes & fees

8.6/10 Excellent! (329 reviews)

Sun N Sound

22 Soundview Drive Montauk NY

3.597.028 ₫

4.532.655 ₫ total

18 Oct - 19 Oct

includes taxes & fees

9.2/10 Wonderful! (334 reviews)

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY

5.481.234 ₫

6.262.310 ₫ total

29 Oct - 30 Oct

includes taxes & fees

Hotels in Wainscott with star rating

Frequently asked questions

What's the weather like in Wainscott?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Wainscott is 1452 mm.

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Find hotels in Wainscott, NY from 3.309.992 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Wainscott

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Wainscott hotels

1. The Sagaponack

2. Topping Rose House

3. The Hedges Inn

4. The Maidstone

5. A Room At The Beach

6. The Huntting Inn

7. Bridgehampton Inn

8. Sag Harbor Inn

9. East Hampton House Resort

10. The 1770 House Restaurant & Inn

11. Journey East Hampton

12. Mill House Inn

13. Faraway Sag Harbor

14. The Roundtree, Amagansett

15. The Reform Club

16. Southampton Inn

17. EHP Resort & Marina

18. Sound View Greenport

19. The Harbor Front Inn

20. Silver Sands Motel & Beach Bungalows

Learn more about Wainscott

Top Wainscott Hotel Reviews

Zey Hotel

Offshore Montauk

Montauk Blue Hotel

Sound View Greenport

The Bentley Hotel Southampton

Ocean Vista Resort

Ocean Surf Resort

More cheap stays in Wainscott

Kenny's Tipperary Inn

The Atlantic Hotel

The Bentley Hotel Southampton

Ocean Surf Resort

Sun N Sound

The Hampton Maid

Hotels in Wainscott with star rating

Frequently asked questions

Explore a world of travel with Expedia

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