Hotels with Swimming Pool, Shelter Island New York

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. Offshore Montauk : Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool, and free self parking. Pier Blue Inn Old Saybrook - Essex : Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport : Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Montauk Manor : Features sun loungers, a seasonal outdoor pool, and complimentary wireless internet access.

A wooden gazebo by a pond with a large tree trunk nearby.

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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.

P6,287 total

includes taxes & fees

Jul 6 - Jul 7

Quality Inn Old Saybrook - Westbrook

Old Saybrook

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

P8,346 total

includes taxes & fees

Jul 26 - Jul 27

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.

P5,689 total

includes taxes & fees

Jul 12 - Jul 13

Water's Edge Resort & Spa

Westbrook Center

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

P22,437 total

includes taxes & fees

Jul 8 - Jul 9

Hyatt Place Long Island East End

Riverhead

Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.

P18,458 total

includes taxes & fees

Jul 7 - Jul 8

Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Old Saybrook Center

Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.

P29,722 total

includes taxes & fees

Jul 21 - Jul 22

Indoor pool, seasonal outdoor pool, sun loungers

Gurney's Montauk Resort & Seawater Spa

Montauk

Plunge into seaside bliss at a beachfront haven with private white sands, seasonal outdoor pool, and indoor swimming sanctuary.

P89,271 total

includes taxes & fees

Jul 19 - Jul 20

Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

Shelter Island Heights

Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.

P50,409 total

includes taxes & fees

Jul 6 - Jul 7

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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

Aqualina Inn Montauk

10/10 Excellent

"Clean room/ great staff/ walking distance to beach."

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. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool, and free self parking. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Montauk Manor: Features sun loungers, a seasonal outdoor pool, and complimentary wireless internet access.

What is there to see and do in Shelter Island?

Explore places like The Hamptons Beaches while you're in the area. Make a point to visit attractions like Sunset Beach and Shelter Island Whale's Tail.

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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