The Best Hotels with a Pool in Wainscott, NY from ₩261,814 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. Montauk Manor : Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. The Atlantic Hotel : Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Bentley Hotel Southampton : Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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Our top choices for Wainscott hotels with a pool

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

The Sagaponack

Wainscott

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

₩782,626 total

includes taxes & fees

Jun 22 - Jun 23

Seasonal outdoor pool, pool umbrellas, sun loungers

Kenny's Tipperary Inn

Culloden Shores

Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.

₩509,231 total

includes taxes & fees

Jun 21 - Jun 22

Breakers Montauk

Montauk

Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.

₩337,244 total

includes taxes & fees

Jun 11 - Jun 12

Aqualina Inn Montauk

Downtown Montauk

Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.

₩311,551 total

includes taxes & fees

Jun 14 - Jun 15

Seasonal outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas

Ocean Surf Resort

Downtown Montauk

Seasonal Montauk retreat with sun-drenched pool deck offering ocean views, just steps from downtown.

₩265,247 total

includes taxes & fees

Jun 10 - Jun 11

Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool umbrellas

Offshore Montauk

Montauk

₩705,136 total

includes taxes & fees

Jun 22 - Jun 23

Ocean Resort Inn

Downtown Montauk

Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.

₩560,759 total

includes taxes & fees

Jun 22 - Jun 23

Sun N Sound

Culloden Shores

Splash into refreshing waters at this beach-adjacent retreat with sun-soaked outdoor pool.

₩261,814 total

includes taxes & fees

Jun 9 - Jun 10

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Choose what matters most at hotels with a pool in Wainscott

Breakfast included

4 stars

Top Wainscott Hotel Reviews

The Hampton Maid

10/10 Excellent

"A absolutely wonderful property to stay at. Only wish was we had more time to stay longer. My only suggestion would be to add a hottub."

Kenny's Tipperary Inn

10/10 Excellent

"The property is very nice, quiet, and quaint. We stayed the night to head out on a fishing charter at 4am, and the location is literally walking distance. The room and property are very clean, and being greeted by very friendly staff was great after a long drive. The beds were comfortable, linens crisp and clean. The ceiling in the bath was a bit dated, but did not take away from a very comfortable stay. I booked through Expedia and the rate was the lowest in the area, and well worth the stay. And, beautiful friendly dogs greeted us. If we go back to Montauk, we will definitely check for rooms here first. Highly recommend."

Gurney's Montauk Resort & Seawater Spa

6/10 Okay

"Almost everything was wonderful but @10:38 guy knock our door ,my husband open gurneys employee he’s telling my husband speak no English ? Is how resort employee cnt speak English n why he’s knocking our door checkout till 11:30 .Pls train employees not to knock for no reason it was scary ."

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. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Bentley Hotel Southampton: Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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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