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Find Hotels with a Pool in Shelter Island, NY

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Top Shelter Island Hotels with a Pool

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (279)
"Great staff and clean rooms"
$78 nightly
The price is $90
Oct 6 - Oct 7
Total with taxes and fees
Clinton Motel

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (346)
"Return visitor. Great stay."
$160 nightly
The price is $183
Nov 2 - Nov 3
Total with taxes and fees
The Bentley Hotel Southampton

New and Modern Bridgehampton Accommodations

2.0 star property
9.6 out of 10, Exceptional, (14)
"Had a great stay here with a small group. Host was very accommodating and responsive. "
$384 nightly
The price is $438
Oct 5 - Oct 6
Total with taxes and fees
New and Modern Bridgehampton Accommodations

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (52)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
$1,165 nightly
The price is $1,331
Oct 5 - Oct 6
Total with taxes and fees
Work and Play Special! Extended Stay Discount

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1252)
"Beautiful grounds, excellent staff"
$143 nightly
The price is $164
Nov 3 - Nov 4
Total with taxes and fees
Montauk Manor

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (194)
"Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!"
$134 nightly
The price is $153
Oct 26 - Oct 27
Total with taxes and fees
Ocean Vista Resort

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1003)
"We have stayed there before so have been pleased with it."
$94 nightly
The price is $108
Nov 2 - Nov 3
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook

Offshore Montauk

2.0 star property
9.2 out of 10, Wonderful, (55)
"The staff is excellent and very accommodating. Great place in a great location. Would stay here again."
$249 nightly
The price is $285
Oct 20 - Oct 21
Total with taxes and fees
Offshore Montauk

Aqualina Inn Montauk

2.5 star property
9.6 out of 10, Exceptional, (481)
"Great location walkable to beach shopping & restaurants."
$123 nightly
The price is $141
Oct 5 - Oct 6
Total with taxes and fees
Aqualina Inn Montauk

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (316)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
$126 nightly
The price is $144
Oct 19 - Oct 20
Total with taxes and fees
Hampton's Vacation 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.

Top Shelter Island Hotel Reviews

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.

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