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

Hotels with Swimming Pools in Wainscott

  • 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 Swimming Pools

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Wainscott hotels with a pool

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.

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
S$344
includes taxes & fees
3 Nov - 4 Nov
The Sagaponack
Outdoor pool
Reception
Room
Terrace/patio

2. 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.
S$232
includes taxes & fees
2 Nov - 3 Nov
East Hampton House Resort
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.
Beach
A bathtub surrounded by candles and flower petals.

3. 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.
S$432
includes taxes & fees
6 Oct - 7 Oct
A Room At The Beach
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 hotel lobby with a sofa, chairs, tables, and a large window.

4. 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.
S$320
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
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.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

5. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.
S$375
includes taxes & fees
18 Oct - 19 Oct
Journey East Hampton
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 covered porch with white railings, green cushioned chairs, hanging flower baskets, and pendant lights.
A dining area with a chandelier, a large table, chairs, and a vase with flowers.

6. 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.
S$600
includes taxes & fees
12 Oct - 13 Oct
Mill House Inn
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 modern hotel room with a bed, bedside table, and a view of the garden.
A bar area with shelves stocked with various bottles and glasses.

7. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
S$845
includes taxes & fees
7 Oct - 8 Oct
Topping Rose House
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A spacious living room with a fireplace, comfortable seating, and large windows.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
S$658
includes taxes & fees
2 Nov - 3 Nov
Faraway Sag Harbor
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 outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

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.
S$210
includes taxes & fees
12 Oct - 13 Oct
The Bentley Hotel Southampton
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 splendour with poolside bar service.
S$313
includes taxes & fees
1 Nov - 2 Nov
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Montauk Yacht Club was the perfect getaway for my boyfriend and I to celebrate our 3 year anniversary. Our room was spotless and had a great view of the water. We did mention to them ahead of time that it was our anniversary, thinking they might have some champagne or something waiting in the room for us, but they did not. Nonetheless, it was still a perfect stay. We played tennis and the courts were beautiful. The on-site restaurant was very yummy as well! I definitely recommend coming during the off season, as it is way less crowded in town and very relaxing."
Sarah 3-night trip
Posted 3 hours ago
Montauk Yacht Club
Sun N Sound

Sun N Sound

8/10 Good
"Everything was fine accept there really wasn’t any privacy people and staff were always by room and outdoor space"
Joseph 2-night trip
Posted 3 hours ago
Sun N Sound
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 8 hours ago
Ocean Surf Resort
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Such a great spot! Clean, easy access, everything you need!!"
Christian 3-night trip
Posted 3 days ago
Ocean Resort Inn
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beachcomber was wonderful loved it"
elizabeth 3-night trip
Posted 4 days ago
Beachcomber Resort at Montauk

Frequently asked questions

What are some accommodation options with pools in Wainscott?
The Sagaponack: B&B located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and sunloungers. 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 that offers an outdoor pool if you plan to visit Wainscott in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.

Explore a world of travel with Expedia