Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Our top choices for Shelter Island hotels with a pool

Exterior

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,294 reviews)
"Nice pool, great restaurant "
United States
April
The price is ￥21,239
￥27,264 total
includes taxes & fees
Feb 16 - Feb 17
Montauk Manor
Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (102 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is ￥17,791
￥29,081 total
includes taxes & fees
Feb 25 - Feb 26
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (885 reviews)
"Big room Clean Needs bathroom update In general, we had a good day"
United States
Raz
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (610 reviews)
"Nice place"
United States
Mateusz
The price is ￥22,983
￥30,672 total
includes taxes & fees
Mar 15 - Mar 16
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (566 reviews)
"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "
United States
Pamela
The price is ￥19,170
￥26,280 total
includes taxes & fees
Feb 17 - Feb 18
The Harbor Front Inn
Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is ￥20,191
￥26,402 total
includes taxes & fees
Feb 17 - Feb 18
Windward Shores Ocean Resort
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (435 reviews)
"Adorable room"
United States
Martin
The price is ￥19,327
￥22,233 total
includes taxes & fees
Feb 24 - Feb 25
The Bentley Hotel Southampton
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is ￥11,953
￥13,746 total
includes taxes & fees
Feb 15 - Feb 16
Clinton Motel
Indoor pool, outdoor pool

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is ￥18,082
￥20,660 total
includes taxes & fees
Mar 3 - Mar 4
Hyatt Place Long Island East End
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is ￥15,500
￥17,825 total
includes taxes & fees
Feb 18 - Feb 19
Quality Inn Old Saybrook - Westbrook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
Ocean view

Top Shelter Island Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Clean cozy always enjoy our stay "
Tim 1-night trip
Posted 5 days ago
Hyatt Place Long Island East End

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. Pier Blue Inn Old Saybrook - Essex: Hotel, 1-minute walk from The Hamptons Beaches. Provides sun loungers, an indoor pool, and complimentary wireless internet access. Montauk Blue Hotel: 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 a seasonal outdoor pool, an indoor 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 Shelter Island Whale's Tail, Mashomack Preserve, and Shell 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 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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