Brioche buns with chocolate chips priced at $3.50.

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Check availability on Wainscott Woods Hotels with Pool

Tonight
1 Sep - 2 Sep
Tomorrow
2 Sep - 3 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Wainscott Woods hotels with a pool

Two people sitting by a poolside with a dining setup including plates, a bottle, and a wine glass.
A hotel room with two beds, a kitchenette, a refrigerator, and a wall-mounted shelf with bottles.
A well-maintained garden with a wooden cabin, a small tree, and a paved pathway.
A modern bathroom with a glass-enclosed shower, a white sink, and a large mirror.

1. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
  • Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.
฿21,456
฿25,672 total
includes taxes & fees
10 Sept - 11 Sept
Wainscott Woods Retreat
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.
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

2. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
฿13,265
฿15,155 total
includes taxes & fees
30 Sept - 1 Oct
A Room At The Beach
A swimming pool with two lounge chairs and a green umbrella.
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.

3. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
฿10,510
฿13,663 total
includes taxes & fees
10 Sept - 11 Sept
The Sagaponack
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A seaside restaurant with outdoor seating, a deck, and a view of the ocean.
A spacious room with wicker furniture, large windows, and a view of the sea.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
฿2,396
฿5,579 total
includes taxes & fees
30 Sept - 1 Oct
Sound View Greenport
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
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 lounge area with a pool view, white furniture, and contemporary lighting fixtures.

5. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
฿5,372
฿6,967 total
includes taxes & fees
9 Sept - 10 Sept
The Bentley Hotel Southampton

6. East Hampton House Resort

East Hampton House Resort
East Hampton North
  • Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
฿8,208
฿10,279 total
includes taxes & fees
28 Sept - 29 Sept
East Hampton House Resort
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 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.

7. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
฿9,978
฿11,400 total
includes taxes & fees
21 Sept - 22 Sept
Sag Harbor Inn
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a grassy area and trees in the background.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

8. Hamlet Inn

Hamlet Inn
Southampton
  • Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
฿4,484
฿5,795 total
includes taxes & fees
30 Sept - 1 Oct
Hamlet Inn
A large indoor swimming pool with multiple lanes, safety signs, and a tiled wall with hexagonal patterns.
A coastal pathway with a wooden bridge leading to a green sports court.
A modern bathroom with a glass shower enclosure, a bathtub, and a wall-mounted faucet.
A wooden deck with Adirondack chairs and tables, overlooking a scenic landscape.

9. Ocean Vista Resort

Ocean Vista Resort
Amagansett
  • Oceanside sanctuary provides splendid private beach access and indoor pool oasis.
฿4,701
฿5,371 total
includes taxes & fees
27 Sept - 28 Sept
Ocean Vista Resort
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.
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.

10. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.
฿11,789
฿14,816 total
includes taxes & fees
28 Sept - 29 Sept
Journey East Hampton
View all properties

Choose what matters most at hotels with a pool in Wainscott Woods

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Wainscott Woods Hotel Reviews

Montauk Yacht Club

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."
Arabella 1-night trip
Posted 15 hours ago
Montauk Yacht Club
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Located right on the beach. Centrally located to shops and restaurants."
Alyce 1-night trip
Posted 19 hours ago
Ocean Surf Resort
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Very clean, the staff was kind and helpful. The restaurant on site was really nice, and the food was delicious. Definitely would stay again."
Gina 2-night trip
Posted 2 days ago
The Hampton Maid
Marram

Marram

10/10 Excellent
"none"
ITALO 1-night trip
Posted 4 days ago
Marram

Frequently asked questions

What are some accommodation options with pools in Wainscott Woods?
Sound View Greenport: Features a private beach, a seasonal outdoor pool and 2 bars. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool and free self parking. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach. Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach.
What is there to see and do in Wainscott Woods?
Make a point to visit attractions such as Georgica Beach and Guild Hall. During your stay, visit sights such as Wolffer Estates Vineyard, The Jewish Center of the Hamptons and East Hampton Main Beach.
When is the best time to book a hotel with a pool in Wainscott Woods?
You may want to consider accommodation with an outdoor swimming pool if you plan to visit Wainscott Woods in the hottest months of August, July or September, when the average temperature is 21°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or March, when the average temperature is 3°C.

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