The Best Hotels with a Pool in Wainscott, NY from ₩188,111 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. Sound View Greenport : Features a private beach, a seasonal outdoor pool, and 2 bars. Montauk Blue Hotel : Hotel, 1-minute walk from The Hamptons Beaches. Offers sun loungers, an indoor pool, and flat-screen televisions.

sunset on the beach in the Hamptons with a cotton candy colored sky

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 a Pool

Tonight

Tomorrow

This weekend

Next weekend

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.

₩338,367 total

includes taxes & fees

Mar 10 - Mar 11

Wainscott Woods Retreat

Wainscott

Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.

₩594,836 total

includes taxes & fees

Mar 10 - Mar 11

Offshore Montauk

Montauk

₩281,528 total

includes taxes & fees

Mar 10 - Mar 11

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Southampton

Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.

₩188,111 total

includes taxes & fees

Mar 10 - Mar 11

Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

The Harbor Front Inn

Greenport

Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.

₩279,525 total

includes taxes & fees

Mar 22 - Mar 23

Montauk Manor

Montauk

Refreshing hilltop retreat with year-round pool access and sweeping ocean vistas.

₩285,343 total

includes taxes & fees

Mar 30 - Mar 31

Windward Shores Ocean Resort

Napeague

Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.

₩282,271 total

includes taxes & fees

Mar 10 - Mar 11

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.

₩221,150 total

includes taxes & fees

Mar 11 - Mar 12

View all properties

Choose what matters most at hotels with a pool in Wainscott

Breakfast included

4 stars

Top Wainscott Hotel Reviews

The Atlantic Hotel

2/10 Terrible

"We expected 2 queen beds we got 2 double beds.The security lock on the door was broken,the smoke/fire alarm was just a wire hanging from the ceiling and the second bath towel was full of suspect stains. The only positive was the gentleman on reception on checking out who listened and apologized and later called to say we would get a refund.We would never recommend this place "

Gurney's Montauk Resort & Seawater Spa

8/10 Good

"I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly disappointed to get a call on our check In day to tell us the indoor pool could not be used. That was literally what we wanted to do for the weekend was relax at the pool and eat and drink. I booked the trips weeks prior so to get a call the day of saying we can’t use to pool during our stay was truly disappointing. They waived the resort fee for the inconvenience, otherwise the weekend was great. "

Kenny's Tipperary Inn

6/10 Okay

"The room was big, and private. Didnt even have to speak with someone to check in or out so that was nice. But I wasn't sure if the sheets werereally changed cause i saw some hairs so that made me uncomfortable. The bathtub was an out of service jacuzzi, which you cant use. Not that i wanted to. But the draw back was i literally had to put my whole body on the counter to get in and out of the shower. A stepping stole wouldve been great. Im 5"2 so it was basically a mountain/hazard getting in and out. My bf is 5"10-6" and he also struggled. I didnt expect a full mini fridge but at least a bottle of water would have been nice. There are vending machines with soda and some chips etc. But no water. It there was water and a stepping stole in the bathroom I'd say its a 4/5."

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. Sound View Greenport: Features a private beach, a seasonal outdoor pool, and 2 bars. Montauk Blue Hotel: Hotel, 1-minute walk from The Hamptons Beaches. Offers sun loungers, an indoor pool, and flat-screen televisions.

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.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Wainscott on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Wainscott Hotels with a Pool