Book the Best Hotels with POOL in Wainscott in 2026

Q: 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.

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Our top choices for Wainscott hotels with a pool

A swimming pool with two lounge chairs and a green umbrella.

1. The Sagaponack

Wainscott

Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.

CA $388 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a wooden fence, a grassy yard, and a white building in the background.

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

Wainscott

CA $2,951 total

includes taxes & fees

Nov 18 - Nov 19

3. 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.

CA $272 total

includes taxes & fees

Nov 17 - Nov 18

A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

4. Journey East Hampton

East Hampton North

Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.

CA $296 total

includes taxes & fees

Nov 24 - Nov 25

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

5. Sag Harbor Inn

Sag Harbor

Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.

CA $353 total

includes taxes & fees

Nov 11 - Nov 12

A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

6. A Room At The Beach

Bridgehampton

Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.

CA $478 total

includes taxes & fees

Nov 16 - Nov 17

A pool area with umbrellas, potted plants, and a pathway leading to a building.

7. Faraway Sag Harbor

Sag Harbor

Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.

CA $575 total

includes taxes & fees

Dec 6 - Dec 7

A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

8. Topping Rose House

Bridgehampton

Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.

CA $984 total

includes taxes & fees

Nov 11 - Nov 12

A house with a sloped roof, large windows, and a pathway leading to the entrance.

9. 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.

CA $663 total

includes taxes & fees

Nov 11 - Nov 12

A clear swimming pool with blue tiles, surrounded by lounge chairs and blue umbrellas.

10. Southampton Inn

Southampton

Sparkling seasonal pool at this Tudor hotel offers summer splendour with poolside bar service.

CA $346 total

includes taxes & fees

Nov 11 - Nov 12

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Choose what matters most at hotels with a pool in Wainscott

Breakfast included

4 stars

Top Wainscott Hotel Reviews

The Sagaponack

Wainscott

10/10 Excellent

Brad

Windward Shores Ocean Resort

Napeague

10/10 Excellent

Anonymous traveller

The Hermitage

Amagansett

10/10 Excellent

Location of hotel right on the dunes and with ocean view and access was perfect. Pristine location from where I could enjoy walking on my beloved beach far from madding crowds proved perfect for my new year's eve, and day, wishes. Accommodation was spacious with all (basic) necessary comforts. Beds were very comfortable. It was clean, though not stylish. I was welcomed warmly, and when a problem with wi-fi access arose, responded to immediately and graciously. This was not the season for...

Philippa

A swimming pool with a white fence, a table with chairs, and a building with a white picket fence in the background.

Southampton Long Island Hotel

Southampton

10/10 Excellent

Christian

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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