Shelter Island Hotels with Swimming Pool

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Check availability on Shelter Island Hotels with Swimming Pools

Our top choices for Shelter Island hotels with a pool

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,282 reviews)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
The price is RM562
RM721 total
includes taxes & fees
29 Jan - 30 Jan
Montauk Manor

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (94 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is RM471
RM769 total
includes taxes & fees
3 Feb - 4 Feb
Offshore Montauk

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (883 reviews)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (607 reviews)
"Nice place"
United States
Mateusz
The price is RM544
RM737 total
includes taxes & fees
21 Jan - 22 Jan
Sound View Greenport

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
The price is RM351
RM453 total
includes taxes & fees
21 Jan - 22 Jan
Hamlet Inn

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (301 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is RM308
RM354 total
includes taxes & fees
21 Jan - 22 Jan
Clinton Motel

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (562 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is RM544
RM737 total
includes taxes & fees
21 Jan - 22 Jan
The Harbor Front Inn

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,003 reviews)
"Was a clean room and the pool was warm and kids had fun. Breakfast was good and plenty of choices "
United States
pieter
The price is RM393
RM452 total
includes taxes & fees
28 Jan - 29 Jan
Quality Inn Old Saybrook - Westbrook

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is RM426
RM507 total
includes taxes & fees
21 Jan - 22 Jan
Southampton Long Island Hotel

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (428 reviews)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is RM492
RM566 total
includes taxes & fees
29 Jan - 30 Jan
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.

Top Shelter Island Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers a seasonal outdoor pool, an indoor pool and a private beach. Montauk Blue Hotel: Provides sunloungers, an indoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex: Offers free self parking, an outdoor pool and complimentary wireless Internet access. Offshore Montauk: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Mashomack Preserve. Discover sights such as Shelter Island Whale's Tail, Crescent Beach and Gardiner's Bay Country Club 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.

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