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

Search Hotels with Pool 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 Pool

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Wainscott hotels with a pool

A swimming pool with two lounge chairs and a green umbrella.
A beach with pebbles and sand, a sunset, and a calm sea.
A wooden building with a white window and a balcony.
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.
Rp4.329.212
Rp5.665.019 total
includes taxes & fees
1 Oct - 2 Oct
The Sagaponack
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A large, white, two-story building with a covered porch and a bicycle parked in front.
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 bar area with shelves stocked with various bottles and glasses.

2. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
Rp11.198.326
Rp12.856.749 total
includes taxes & fees
4 Oct - 5 Oct
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 spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A hotel lobby with a sofa, chairs, tables, and a large window.

3. 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.
Rp4.476.522
Rp5.114.427 total
includes taxes & fees
30 Oct - 31 Oct
Sag Harbor Inn
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 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.

4. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.
Rp4.489.177
Rp5.641.805 total
includes taxes & fees
12 Oct - 13 Oct
Journey East Hampton
Outdoor pool
Living area
Reception
Room

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.
Rp2.750.634
Rp3.631.376 total
includes taxes & fees
28 Oct - 29 Oct
East Hampton House Resort
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.

6. 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.
Rp2.205.918
Rp3.033.892 total
includes taxes & fees
6 Oct - 7 Oct
The Bentley Hotel Southampton
Pool
Terrace/patio
Room
Living area

7. Windward Shores Ocean Resort

Windward Shores Ocean Resort
Napeague
  • Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.
Rp2.138.483
Rp2.932.032 total
includes taxes & fees
12 Oct - 13 Oct
Windward Shores Ocean Resort
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bathtub surrounded by candles and flower petals.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

8. 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.
Rp5.301.078
Rp6.056.406 total
includes taxes & fees
4 Oct - 5 Oct
A Room At The Beach
A swimming pool with a white fence, a table with chairs, and a building with a white picket fence in the background.
A covered patio area with outdoor seating, a potted plant, and a well-maintained lawn.
A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.
A bedroom with a bed, bedside tables, a chair, a desk, and a bathroom visible through an open door.

9. Southampton Long Island Hotel

Southampton Long Island Hotel
Southampton
  • Luxurious poolside retreat with seasonal outdoor oasis and plush sun loungers, just minutes from Cooper's Beach in the Hamptons.
Rp2.846.577
Rp3.394.767 total
includes taxes & fees
5 Oct - 6 Oct
Southampton Long Island Hotel
A swimming pool with lounge chairs and a table, surrounded by greenery and buildings.
A beach with sand and sparse vegetation.
A bedroom with a large bed, a chandelier, and multiple windows.
A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

10. The Hampton Maid

The Hampton Maid
Hampton Bays
  • Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
Rp3.802.347
Rp4.344.181 total
includes taxes & fees
13 Oct - 14 Oct
The Hampton Maid
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

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Bathroom in my unit was kind of outdated but still adequate Seen another unit and it was updated beautifully"
John 2-night trip
Posted 2 days ago
Ocean Surf Resort
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Great resort for a good price. On the beach."
Thomas 2-night trip
Posted 2 days ago
Ocean Vista Resort
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 2 weeks ago
Faraway Sag Harbor

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