Brioche buns with chocolate chips priced at $3.50.

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Check availability on Wainscott Woods Hotels with Pool

Tonight
3 Sep - 4 Sep
Tomorrow
4 Sep - 5 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 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 patio with four wicker chairs and a table, a blue umbrella, and a wooden building in the background.

1. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
  • Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.
16.895.304 ₫
20.215.440 ₫ total
includes taxes & fees
10 Sept - 11 Sept
Wainscott Woods Retreat
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.
A bathtub surrounded by candles and flower petals.

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.
8.578.346 ₫
9.800.695 ₫ total
includes taxes & fees
4 Oct - 5 Oct
A Room At The Beach
A swimming pool with two lounge chairs and a green umbrella.
A wooden building with a white window and a balcony.
A beach with pebbles and sand, a sunset, and a calm sea.
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

3. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
6.618.103 ₫
8.864.882 ₫ total
includes taxes & fees
4 Oct - 5 Oct
The Sagaponack
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A spacious room with wicker furniture, large windows, and a view of the sea.
A seaside restaurant with outdoor seating, a deck, and a view of the ocean.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
6.355.537 ₫
9.495.483 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Sound View Greenport

5. 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.
6.453.068 ₫
8.081.588 ₫ total
includes taxes & fees
28 Sept - 29 Sept
East Hampton House Resort
A large indoor swimming pool with multiple lanes, safety signs, and a tiled wall with hexagonal patterns.
Two Adirondack chairs facing a beach with a clear view of the ocean.
A wooden deck with Adirondack chairs and tables, overlooking a scenic landscape.
A coastal pathway with a wooden bridge leading to a green sports court.

6. Ocean Vista Resort

Ocean Vista Resort
Amagansett
  • Oceanside sanctuary provides splendid private beach access and indoor pool oasis.
3.304.880 ₫
3.776.037 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Ocean Vista Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
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.

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.
7.845.366 ₫
8.963.330 ₫ total
includes taxes & fees
23 Sept - 24 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 house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.
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 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.

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.
3.304.753 ₫
4.271.540 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Hamlet Inn
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
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.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

9. 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.
3.765.139 ₫
4.953.520 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Bentley Hotel Southampton
A modern living room with a sofa, a coffee table, a TV mounted on the wall, and large windows.

10. Sea Crest Resort

Sea Crest Resort
Amagansett
  • Coastal serenity awaits at this oceanfront hotel with an inviting pool and comfortable loungers for relaxation.
4.329.422 ₫
5.513.396 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Sea Crest Resort
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

The Hampton Maid

The Hampton Maid

10/10 Excellent
"wonderful hotel."
SABINA 1-night trip
Posted 8 hours ago
The Hampton Maid
Ocean Surf Resort

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"
naoko 1-night trip
Posted 10 hours ago
Ocean Surf Resort
Kenny's Tipperary Inn

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."
Demetra 4-night trip
Posted 11 hours ago
Kenny's Tipperary Inn
Faraway Sag Harbor

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."
Claudia 3-night trip
Posted 13 hours ago
Faraway Sag Harbor
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great beachfront property! Spa is amazing!"
Daniel 1-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa
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 2 days ago
Montauk Yacht Club

Frequently asked questions

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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