Photo by tom owens

Find Hotels with a Pool in Shelter Island, NY

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 a Pool

Top Shelter Island Hotels with a Pool

Clinton Motel
Seasonal outdoor pool
Clinton Motel
2.5 star property
8.6 out of 10, Excellent, (282)
"Great staff and clean rooms"
The price is ₩111,157
₩127,831 total
includes taxes & fees
Oct 15 - Oct 16
Clinton Motel
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn
2.0 star property
8.4 out of 10, Very Good, (864)
"Love this place. "
The price is ₩164,968
₩196,006 total
includes taxes & fees
Oct 16 - Oct 17
Kenny's Tipperary Inn
Montauk Blue Hotel
Indoor pool, open 10:00 AM to 6:00 PM, sun loungers
Montauk Blue Hotel
2.0 star property
9.2 out of 10, Wonderful, (159)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
The price is ₩169,586
₩193,752 total
includes taxes & fees
Nov 9 - Nov 10
Montauk Blue Hotel
A Wave Inn
Front of property
A Wave Inn
2.5 star property
7.4 out of 10, Good, (132)
"A block from the beach, shopping, and dining."
The price is ₩156,176
₩289,650 total
includes taxes & fees
Oct 15 - Oct 16
A Wave Inn
Montauk Manor
Exterior
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1253)
"Beautiful grounds, excellent staff"
The price is ₩179,561
₩233,044 total
includes taxes & fees
Nov 3 - Nov 4
Montauk Manor
Offshore Montauk
BBQ/picnic area
Offshore Montauk
2.0 star property
9.2 out of 10, Wonderful, (59)
"Great place "
The price is ₩216,756
₩410,461 total
includes taxes & fees
Oct 27 - Oct 28
Offshore Montauk
Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (1009)
"We have stayed there before so have been pleased with it."
The price is ₩133,246
₩153,233 total
includes taxes & fees
Nov 2 - Nov 3
Quality Inn Old Saybrook - Westbrook
Ocean Surf Resort
Street view
Ocean Surf Resort
2.0 star property
8.4 out of 10, Very Good, (217)
"Beach view "
The price is ₩188,048
₩214,845 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Surf Resort
Ocean Vista Resort
Indoor pool, a waterfall pool
Ocean Vista Resort
2.5 star property
9.0 out of 10, Wonderful, (196)
"Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back."
The price is ₩191,105
₩218,338 total
includes taxes & fees
Oct 26 - Oct 27
Ocean Vista 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

Marram

Marram

10/10 Excellent
"We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful. "
Josefina 1-night trip
Posted 10 hours ago
Marram

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Provides buffet, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Offers 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: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking.
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 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.