TOP Hotels with Pool in Shelter Island, NY for 2026

Q: What are some accommodation options with pools in Shelter Island?

Pier Blue Inn Old Saybrook - Essex : Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Gurney's Montauk Resort & Seawater Spa : Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool and free self parking. Offshore Montauk : Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa : Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport : Hotel, 1-minute walk from The Hamptons Beaches. Features sunloungers, an indoor pool and complimentary wireless Internet access.

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Our top choices for Shelter Island hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.

1. The Harbor Front Inn

Greenport

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

Rp3.590.053 total

includes taxes & fees

29 Nov - 30 Nov

A poolside area with sun loungers, a pool, and a building with a balcony.

2. Oyster Estate

Greenport

Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.

Rp4.284.742 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.

3. Sound View Greenport

Greenport

Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.

Rp3.708.546 total

includes taxes & fees

11 Nov - 12 Nov

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

4. Sag Harbor Inn

Sag Harbor

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

Rp4.526.004 total

includes taxes & fees

11 Nov - 12 Nov

A two-story building with a swimming pool, red lounge chairs, and a well-maintained lawn.

5. Seven - A Resort Style Inn

Shelter Island Heights

Rp7.867.806 total

includes taxes & fees

24 Nov - 25 Nov

A poolside area with a hat and towel on a lounge chair.

6. North Fork Resort

Greenport

Rp6.638.735 total

includes taxes & fees

19 Nov - 20 Nov

7. Cliffside Resort Condominiums

Greenport

Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.

Rp5.975.465 total

includes taxes & fees

26 Nov - 27 Nov

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

8. Faraway Sag Harbor

Sag Harbor

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

Rp7.364.031 total

includes taxes & fees

7 Dec - 8 Dec

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

9. Water's Edge Resort & Spa

Westbrook Center

Pristine waters await at this coastal retreat with private beach access and year-round pools.

Rp3.696.104 total

includes taxes & fees

12 Nov - 13 Nov

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

10. A Room At The Beach

Bridgehampton

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

Rp6.117.975 total

includes taxes & fees

11 Nov - 12 Nov

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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included

4 stars

Top Shelter Island Hotel Reviews

Cliffside Resort Condominiums

Greenport

10/10 Excellent

Debbie

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

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

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

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 poolside area with lounge chairs, umbrellas, and a view of boats in the background.

Hyatt Place Long Island East End

Riverhead

10/10 Excellent

Beautiful hotel ,staff very efficient and friendly lifts to the rooms were very fast Lovely size room with very comfortable beds ,lovely view over the pool and the lake from the room. Breakfast was not included in our booking but we paid for the breakfast in the hotel which was very filling and varied each morning plenty of coffee available also fresh fruit pancakes and eggs. Plenty of information at reception of what was popular in the area Winery visits were popular The hotel has a ...

Anonymous traveller

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

Journey East Hampton

East Hampton North

10/10 Excellent

Natalie

Frequently Asked Questions

What are some accommodation options with pools in Shelter Island?

Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool and free self parking. Offshore Montauk: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Features sunloungers, an indoor pool and complimentary wireless Internet access.

What is there to see and do in Shelter Island?

Surround yourself with nature at Mashomack Preserve and Sunset Beach. Discover sights such as Shelter Island Historical Society, Wades Beach and Crescent Beach during your stay.

When is the best time to book a hotel with a pool in Shelter Island?

You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.

Search Hotels with Pool in Shelter Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shelter Island hotels with a pool

1. The Harbor Front Inn

2. Oyster Estate

3. Sound View Greenport

4. Sag Harbor Inn

5. Seven - A Resort Style Inn

6. North Fork Resort

7. Cliffside Resort Condominiums

8. Faraway Sag Harbor

9. Water's Edge Resort & Spa

10. A Room At The Beach

Choose what matters most at hotels with a pool in Shelter Island

Top Shelter Island Hotel Reviews

Cliffside Resort Condominiums

10/10 Excellent

Frequently Asked Questions

What are some accommodation options with pools in Shelter Island?

What is there to see and do in Shelter Island?

When is the best time to book a hotel with a pool in Shelter Island?