The Best Hotels with a Pool in Shelter Island, NY from AED 594 in 2026

Q: What are some accommodations with pools in Shelter Island?

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. Montauk Manor : Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. The Atlantic Hotel : Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Bentley Hotel Southampton : Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Montauk Yacht Club : Hotel, 5-minute walk from The Hamptons Beaches. Offers 2 outdoor pools, a children's pool, and a private beach.

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Our top choices for Shelter Island hotels with a pool

Clinton Motel

Clinton

Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.

AED 372 total

includes taxes & fees

7 Jun - 8 Jun

Breakers Montauk

Montauk

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

AED 795 total

includes taxes & fees

7 Jun - 8 Jun

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.

AED 644 total

includes taxes & fees

9 Jun - 10 Jun

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Old Saybrook

Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.

AED 478 total

includes taxes & fees

21 Jun - 22 Jun

Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.

AED 340 total

includes taxes & fees

16 Jun - 17 Jun

Aqualina Inn Montauk

Downtown Montauk

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

AED 608 total

includes taxes & fees

9 Jun - 10 Jun

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.

AED 594 total

includes taxes & fees

10 Jun - 11 Jun

North Fork Resort

Greenport

AED 1,159 total

includes taxes & fees

17 Jun - 18 Jun

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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

The Atlantic Hotel

6/10 Okay

"Hotel is fine if you are just there for a night, maybe two, but the room, especially the carpet, need some major updates."

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 ."

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Frequently asked questions

What are some accommodations with pools in Shelter Island?

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. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Bentley Hotel Southampton: Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Offers 2 outdoor pools, a children's pool, and a private beach.

What is there to see and do in Shelter Island?

Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Gardiner's Bay Country Club, Shelter Island Historical Society, and Havens House during your stay.

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

You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging 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 38°F.

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