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Find Hotels with a Pool in Wainscott, NY

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Check availability on Wainscott Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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.
A wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
₩256,759
₩346,253 total
includes taxes & fees
Oct 28 - Oct 29
The Sagaponack
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar area with shelves stocked with various bottles and glasses.
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.

2. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
₩827,593
₩950,156 total
includes taxes & fees
Oct 25 - Oct 26
Topping Rose House
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.

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.
₩391,767
₩447,588 total
includes taxes & fees
Oct 26 - Oct 27
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 Harbor retreat with a seasonal outdoor pool and balcony views.
₩289,757
₩331,048 total
includes taxes & fees
Nov 1 - Nov 2
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 living room with a fireplace, two sofas, a coffee table, and a chair.
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

5. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
₩304,309
₩382,443 total
includes taxes & fees
Oct 26 - Oct 27
Journey East Hampton
Outdoor pool
Terrace/patio
Living area
Reception

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.
₩191,614
₩254,946 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 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.

7. 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.
₩430,004
₩621,482 total
includes taxes & fees
Oct 26 - Oct 27
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 dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
₩464,404
₩583,637 total
includes taxes & fees
Nov 22 - Nov 23
Faraway Sag Harbor
A clear swimming pool with blue tiles, surrounded by lounge chairs and blue umbrellas.
A well-maintained garden with a central pathway leading to a house.
A snow-covered pathway leading to a building with a porch.
Restaurant

9. Southampton Inn

Southampton Inn
Southampton
  • Sparkling seasonal pool at this Tudor hotel offers summer splendor with poolside bar service.
₩264,618
₩323,879 total
includes taxes & fees
Nov 1 - Nov 2
Southampton Inn
A swimming pool with lounge chairs and a sign indicating a depth of 4 feet.
A spacious interior with a wooden staircase, a blue sofa, and a white chair.
A modern kitchen with a wooden countertop, a black sink, and a pendant light.
A waterfront restaurant with wooden tables and white chairs, set against a backdrop of a marina and calm water.

10. EHP Resort & Marina

EHP Resort & Marina
East Hampton
  • Seasonal outdoor pool flanked by sun loungers invites leisurely afternoons, with poolside cocktail service just steps away.
₩380,388
₩478,059 total
includes taxes & fees
Nov 1 - Nov 2
EHP Resort & Marina
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 Vista Resort

Ocean Vista Resort

10/10 Excellent
"The location could not be more perfect! Right on the beach! The rooms are beautiful and spacious. We had to check in late and it could not be easier. We are really looking forward to our next stay here!"
Stefan 1-night trip
Posted 9 hours ago
Ocean Vista Resort
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Always an amazing stay at Gurneys. The ocean views and the restorative spa alone make this place so special. The staff is friendly and the rooms are kept so clean. Highly recommended."
Peter 2-night trip
Posted 17 hours ago
Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
Svetlana 4-night trip
Posted 1 day ago
Montauk Yacht Club
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."
Joan 2-night trip
Posted 1 day ago
Faraway Sag Harbor
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"Lovely view of the ocean. Bathroom was fine. Room was updated. Only had one nightstand and lamp."
harriet 2-night trip
Posted 2 days ago
Ocean Surf Resort
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 4 days ago
The Atlantic Hotel

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.

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