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

Find Hotels with a Pool in Wainscott, NY

  • 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

Check availability on Wainscott Hotels with a Pool

Tonight
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Wainscott hotels with a pool

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.

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
￥30,665
￥41,353 total
includes taxes & fees
Oct 26 - Oct 27
The Sagaponack
A swimming pool with a wooden fence, a grassy yard, and a white building in the background.
A kitchen with a central island, white cabinetry, and a brick accent wall.
A spacious living room with a white fireplace, a large mirror, and a view of the outdoors.
A spacious living room with a white sofa, a coffee table, and a dining area with a table and chairs.

2. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
￥170,662
￥366,675 total
includes taxes & fees
Nov 16 - Nov 17
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
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 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.

3. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
￥91,923
￥105,576 total
includes taxes & fees
Nov 4 - Nov 5
Topping Rose House
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

4. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
￥34,606
￥39,538 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
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.
Beach

5. 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.
￥46,790
￥53,457 total
includes taxes & fees
Oct 21 - Oct 22
A Room At The Beach
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 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.

6. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
￥37,688
￥47,364 total
includes taxes & fees
Nov 4 - Nov 5
Journey East Hampton
Outdoor pool
Living area
Reception
Room

7. 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.
￥22,914
￥30,488 total
includes taxes & fees
Nov 2 - Nov 3
East Hampton House Resort
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 covered porch with white railings, green cushioned chairs, hanging flower baskets, and pendant lights.

8. Mill House Inn

Mill House Inn
Pantigo Road Historic District
  • Soak in serene poolside moments at this charming Colonial B&B with a garden terrace for ultimate relaxation.
￥51,357
￥74,226 total
includes taxes & fees
Oct 21 - Oct 22
Mill House Inn
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.

9. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
￥58,309
￥73,280 total
includes taxes & fees
Nov 16 - Nov 17
Faraway Sag Harbor
A clear swimming pool with blue tiles, surrounded by lounge chairs and blue umbrellas.
A snow-covered pathway leading to a building with a porch.
Restaurant
A well-maintained garden with a central pathway leading to a house.

10. Southampton Inn

Southampton Inn
Southampton
  • Sparkling seasonal pool at this Tudor hotel offers summer splendor with poolside bar service.
￥31,604
￥38,682 total
includes taxes & fees
Nov 1 - Nov 2
Southampton Inn
View all properties

Choose what matters most at hotels with a pool in Wainscott

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Wainscott Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 6 hours ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

8/10 Good
"This was our third stay at Soundview. We stay there because all of the rooms face the sound and the natural view can’t be beat. The rooms are lodgy but spacious and depending on your room, there are public/private balconies."
Danielle 1-night trip
Posted 1 day ago
Sound View Greenport
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Great place in Montauk. Beautiful view and room was spacious."
fred 4-night trip
Posted 3 days ago
Beachcomber Resort at Montauk

Frequently asked questions

What are some accommodations with pools in Wainscott?
The Sagaponack: B&B located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. 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. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool, and free self parking. The Atlantic Hotel: Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars.
What is there to see and do in Wainscott?
The picturesque setting of The Hamptons Beaches showcases the area's natural beauty. Discover sights such as Georgica Beach, Wolffer Estates Vineyard, and East Hampton Main Beach during your stay. Take in the natural beauty of Wainscott with the beaches.
When is the best time to book a hotel with a pool in Wainscott?
You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Wainscott in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.

Explore a world of travel with Expedia