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Hotels with Pool & Resorts in Shelter Island from AU$126

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Check availability on Shelter Island Hotels with Pool

Best Shelter Island Hotels with Pool

Outdoor pool, a heated pool
Work and Play Special! Extended Stay Discount
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$2,073
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
Seasonal outdoor pool
Clinton Motel
Clinton Motel
2.5 star property
8.6 out of 10, Excellent, (286)
"Great staff and clean rooms"
United States
Tyler
The price is AU$138
includes taxes & fees
28 Oct - 29 Oct
Clinton Motel
Indoor pool, open 10:00 AM to 6:00 PM, pool loungers
Montauk Blue Hotel
Montauk Blue Hotel
2.0 star property
9.2 out of 10, Wonderful, (165)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
United States
Jason
The price is AU$209
includes taxes & fees
9 Nov - 10 Nov
Montauk Blue Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn
Kenny's Tipperary Inn
2.0 star property
8.4 out of 10, Very good, (868)
"Love this place. "
United States
Susan
Kenny's Tipperary Inn
Exterior
Montauk Manor
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1256)
"Beautiful grounds, excellent staff"
United States
Jess
The price is AU$295
includes taxes & fees
3 Nov - 4 Nov
Montauk Manor
Street view
Ocean Surf Resort
Ocean Surf Resort
2.0 star property
8.4 out of 10, Very good, (220)
"Everything was great "
United States
Darryl
The price is AU$215
includes taxes & fees
23 Oct - 24 Oct
Ocean Surf Resort
BBQ/picnic Area
Offshore Montauk
Offshore Montauk
2.0 star property
9.4 out of 10, Exceptional, (62)
"Great place "
United States
Kevin
The price is AU$437
includes taxes & fees
6 Nov - 7 Nov
Offshore Montauk
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
7.2 out of 10, Good, (456)
"the so-called breakfast was absolute minimum only thing available was make your own waffle"
United States
Brian
The price is AU$126
includes taxes & fees
28 Oct - 29 Oct
Econo Lodge Inn & Suites Old Saybrook Westbrook
Front of property
A Wave Inn
A Wave Inn
2.5 star property
7.4 out of 10, Good, (133)
"It’s was a really nice place for the price, everything is walking distance, nice spot."
United States
Giordan
The price is AU$264
includes taxes & fees
3 Nov - 4 Nov
A Wave Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn
Hamlet Inn
2.0 star property
8.6 out of 10, Excellent, (431)
"A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. "
United States
Michelle
The price is AU$212
includes taxes & fees
3 Nov - 4 Nov
Hamlet Inn
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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Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"We love the stay everything was perfect"
angelica 1-night trip
Posted 8 days ago
Water's Edge Resort & Spa

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. Features sunloungers, an indoor pool and complimentary wireless Internet access. Montauk Blue Hotel: Hotel, 6-minute walk from The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool and sunloungers. Marram: Features 2 outdoor swimming pools, an indoor pool and a full-service spa. Saybrook Point Resort & Marina: Offers a private beach, a seasonal outdoor pool and 2 bars.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Mashomack Preserve, Gardiner's Bay Country Club and Shelter Island Historical Society 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.