Search Hotels with Swimming Pool in Shelter Island

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Check availability on Shelter Island Hotels with Swimming Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

The Hermitage

The Hermitage
3.5 star property
Amagansett
9.2 out of 10, Wonderful, (166 reviews)
"Beautifully situated on dunes and beach. Attentive staff, Apartments are well appointed."
United States
Anthony
The price is ₹14,338
₹19,393 total
includes taxes & fees
1 Apr - 2 Apr
The Hermitage
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool 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 ₹8,506
₹9,782 total
includes taxes & fees
29 Mar - 30 Mar
Quality Inn Old Saybrook - Westbrook
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (468 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is ₹6,154
₹7,077 total
includes taxes & fees
23 Mar - 24 Mar
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (303 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is ₹7,161
₹8,235 total
includes taxes & fees
24 Mar - 25 Mar
Clinton Motel
Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,003 reviews)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is ₹24,980
₹31,022 total
includes taxes & fees
23 Mar - 24 Mar
Saybrook Point Resort & Marina
Exterior

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,004 reviews)
"Great place!"
United States
Laura
The price is ₹15,515
₹19,426 total
includes taxes & fees
1 Apr - 2 Apr
Water's Edge Resort & Spa
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (457 reviews)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ₹9,006
₹11,641 total
includes taxes & fees
12 Mar - 13 Mar
Hamlet Inn
Seasonal outdoor pool

Budget Host East End

Budget Host East End
2.0 star property
Riverhead
6.6 out of 10, (799 reviews)
"Easy check in/out. Room was clean. Nice quiet stay. "
United States
Joseph
The price is ₹8,997
₹10,279 total
includes taxes & fees
12 Mar - 13 Mar
Budget Host East End
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, (1,006 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is ₹10,062
₹11,496 total
includes taxes & fees
22 Mar - 23 Mar
Hyatt Place Long Island East End
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, (446 reviews)
"Adorable room"
United States
Martin
The price is ₹12,313
₹14,160 total
includes taxes & fees
28 Mar - 29 Mar
The Bentley Hotel Southampton
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
4 stars

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"This was my first time at Water’s Edge and will definitely not be my last. Our stay was wonderful. Becky at the front desk was "
Jenifer 1-night trip
Posted 4 days ago
Water's Edge Resort & Spa

Frequently asked questions

What are some accommodation options 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. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Offers an indoor pool, an outdoor pool and 2 bars. Hyatt Place Long Island East End: Hotel, 1-minute walk from The Hamptons Beaches. Features sunloungers, an indoor pool and flat-screen televisions.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Wades Beach. Discover sights such as Shelter Island Whale's Tail, Mashomack Preserve 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.