TOP Hotels with Pool in Wainscott Woods, NY for 2026

Q: What are some accommodation options with pools in Wainscott Woods?

Gurney's Montauk Resort & Seawater Spa : Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Offshore Montauk : Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool and free self parking. The Atlantic Hotel : Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. 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 sunloungers, an indoor pool and complimentary wireless Internet access.

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Our top choices for Wainscott Woods hotels with a pool

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

1. Sag Harbor Inn

Sag Harbor

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

฿8,373 total

includes taxes & fees

8 Nov - 9 Nov

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

2. Faraway Sag Harbor

Sag Harbor

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

฿13,627 total

includes taxes & fees

6 Dec - 7 Dec

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

3. Topping Rose House

Bridgehampton

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

฿24,032 total

includes taxes & fees

9 Nov - 10 Nov

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.

฿9,274 total

includes taxes & fees

22 Nov - 23 Nov

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

5. The Sagaponack

Wainscott

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

฿9,232 total

includes taxes & fees

8 Nov - 9 Nov

6. 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.

฿6,437 total

includes taxes & fees

10 Nov - 11 Nov

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

7. A Room At The Beach

Bridgehampton

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

฿11,321 total

includes taxes & fees

8 Nov - 9 Nov

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

8. Southampton Inn

Southampton

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

฿8,192 total

includes taxes & fees

9 Nov - 10 Nov

A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.

9. The Bentley Hotel Southampton

Southampton

Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.

฿5,492 total

includes taxes & fees

14 Nov - 15 Nov

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

10. 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.

฿15,719 total

includes taxes & fees

8 Nov - 9 Nov

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Choose what matters most at hotels with a pool in Wainscott Woods

Breakfast included

4 stars

Top Wainscott Woods Hotel Reviews

Journey East Hampton

East Hampton North

10/10 Excellent

Natalie

Faraway Sag Harbor

Sag Harbor

10/10 Excellent

Thoroughly enjoyed my stay at Baron's Cove. I stayed late February so the pool was closed, but this was expected. It's a motel style hotel where your door opens to the outside, but given the location of the hotel i felt perfectly safe. The Staff were fantastic, and always helpful. The breakfast was first class too. Sag Harbor is such an iconic place within the Hamptons and this hotel is just as iconic in my eyes. The decor, is photo-worthy. I certainly hope to come back again soon!

Nathan

The Bentley Hotel Southampton

Southampton

10/10 Excellent

James

A Room At The Beach

Bridgehampton

8/10 Good

Travelled with a friend at the end of Sept . Quiet time for the hotel which is lovely. Good points : stunning garden! Amount of work that it takes to maintain such beautiful plants is impressive . Stylish outdoor furnitures . Bed and pillows were very comfortable . Had a great night sleep . Free water and rose which was a nice touch Improvement points : Eventhough it’s off season , one of the more pricey hotels I’ve ever stayed in prob because of the location .With that price point , there...

Vee Han

The Sagaponack

Wainscott

10/10 Excellent

Kerry

Mill House Inn

Pantigo Road Historic District

10/10 Excellent

Anna

Southampton Inn

Southampton

10/10 Excellent

Sinead

A poolside area with lounge chairs, a table with food and drinks, and a pool.

Canoe Place Inn and Cottages

Hampton Bays

10/10 Excellent

Ann marie

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

8/10 Good

Suzanne

A swimming pool with lounge chairs and a table, surrounded by greenery and buildings.

The Hampton Maid

Hampton Bays

10/10 Excellent

We had a lovely 3 night stay at this beautiful traditional family owned property (2 rooms/cabins). It was a perfect reset after 5 nights spent in NYC, the surroundings were so peaceful and well maintained as were the rooms. Great to see some local wildlife on the grounds at times too. Staff were friendly and helpful, parking is conveniently located beside each room, making it easy for luggage etc. Daily maid service, rooms were immaculately clean. We had breakfast at the property on one of the...

Sharon

A swimming pool with lounge chairs and umbrellas, surrounded by a white building with multiple windows.

Offshore Montauk

Montauk

10/10 Excellent

michaela

Frequently Asked Questions

What are some accommodation options with pools in Wainscott Woods?

Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool and free self parking. The Atlantic Hotel: Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. 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 sunloungers, an indoor pool and complimentary wireless Internet access.

What is there to see and do in Wainscott Woods?

Make a point to visit attractions such as Georgica Beach and Guild Hall. During your stay, visit sights such as Wolffer Estates Vineyard, The Jewish Center of the Hamptons and East Hampton Main Beach.

When is the best time to book a hotel with a pool in Wainscott Woods?

You may want to consider accommodation with an outdoor swimming pool if you plan to visit Wainscott Woods in the hottest months of August, July or September, when the average temperature is 21°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or March, when the average temperature is 3°C.

Search Hotels with Pool in Wainscott Woods

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wainscott Woods hotels with a pool

1. Sag Harbor Inn

2. Faraway Sag Harbor

3. Topping Rose House

4. Journey East Hampton

5. The Sagaponack

6. East Hampton House Resort

7. A Room At The Beach

8. Southampton Inn

9. The Bentley Hotel Southampton

10. Mill House Inn

Choose what matters most at hotels with a pool in Wainscott Woods

Top Wainscott Woods Hotel Reviews

Journey East Hampton

10/10 Excellent

Frequently Asked Questions

What are some accommodation options with pools in Wainscott Woods?

What is there to see and do in Wainscott Woods?

When is the best time to book a hotel with a pool in Wainscott Woods?