Photo by tom owens

Search Hotels with Swimming Pool in Shelter Island

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island Hotels with Swimming Pool

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Shelter Island Hotels with Swimming Pool

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, (170)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
United States
Jason
The price is ₹10,454
₹11,944 total
includes taxes & fees
9 Nov - 10 Nov
Montauk Blue Hotel
Seasonal outdoor pool
Clinton Motel
Clinton Motel
2.5 star property
8.6 out of 10, Excellent, (287)
"Great staff and clean rooms"
United States
Tyler
The price is ₹6,852
₹7,880 total
includes taxes & fees
18 Nov - 19 Nov
Clinton Motel
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 ₹6,284
₹7,227 total
includes taxes & fees
18 Nov - 19 Nov
Econo Lodge Inn & Suites Old Saybrook Westbrook
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, (869)
"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, (1257)
"Beautiful grounds, excellent staff"
United States
Jess
The price is ₹13,283
₹16,897 total
includes taxes & fees
4 Nov - 5 Nov
Montauk Manor
Indoor pool, 2 outdoor pools
Montauk Yacht Club
Montauk Yacht Club
4.0 star property
8.6 out of 10, Excellent, (1005)
"Wonderful hotel and location "
United States
FIONA
Montauk Yacht Club
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, (432)
"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 ₹9,409
₹12,161 total
includes taxes & fees
2 Nov - 3 Nov
Hamlet Inn
BBQ/picnic Area
Offshore Montauk
Offshore Montauk
2.0 star property
9.4 out of 10, Exceptional, (63)
"Great place "
United States
Kevin
The price is ₹13,230
₹25,152 total
includes taxes & fees
9 Nov - 10 Nov
Offshore Montauk
Front of property
Sea Crest Resort
Sea Crest Resort
2.5 star property
9.2 out of 10, Wonderful, (498)
"Perfect location!"
United States
Bernadette
The price is ₹15,074
₹19,133 total
includes taxes & fees
9 Nov - 10 Nov
Sea Crest Resort
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.
View all properties

Top Shelter Island Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Breakfast and the Halyard restaurant are top shelf. A few quirks with our room(s) - no cable service, a locked bathroom door that couldn’t be opened, and a dead bolt that didn’t work- but the staff were helpful and accommodating and did everything they could to make things right."
Kirsten 2-night trip
Posted 22 hours ago
Sound View Greenport

Explore a world of travel with Expedia

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.