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Find Hotels with a Pool in Shelter Island Heights, NY

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Check availability on Shelter Island Heights Hotels with a Pool

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Shelter Island Heights hotels with a pool

BBQ/picnic area
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (83)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is ￥18,315
￥29,936 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (879)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1270)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is ￥21,864
￥28,067 total
includes taxes & fees
Dec 23 - Dec 24
Montauk Manor
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
2.5 star property
Niantic
9.0 out of 10, Wonderful, (451)
"Easy check in and check out, comfortable bed, clean"
United States
Eric
The price is ￥14,575
￥16,761 total
includes taxes & fees
Dec 29 - Dec 30
Best Western Niantic - New London/Mystic Area
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (548)
"Awesome stay!!! Great Location "
United States
Bryan
The price is ￥21,155
￥31,890 total
includes taxes & fees
Dec 23 - Dec 24
The Harbor Front Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (462)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveler
The price is ￥10,574
￥12,160 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (599)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is ￥25,114
￥36,415 total
includes taxes & fees
Dec 23 - Dec 24
Sound View Greenport
Indoor pool, a heated pool
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
2.5 star property
Niantic
8.4 out of 10, Very Good, (1000)
"Clean Room/Polite staff/ Breakfast was basic/ pool area looked maintained."
United States
Sara
The price is ￥12,798
￥14,718 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sleep Inn & Suites Niantic North
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (401)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ￥19,739
￥22,710 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Bentley Hotel Southampton
Sports facility
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is ￥22,579
￥41,837 total
includes taxes & fees
Dec 28 - Dec 29
Hero Beach Club
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 Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything was wonderful. Staff was friendly, very clean,we enjoyed it."
Donna 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa

Frequently asked questions

What's it like visiting Shelter Island Heights?
If lounging by a pool is your idea of a great vacation, you may want to check out Shelter Island Heights, which has 10 places to stay with pools. While you're visiting, you can explore sights such as Sunset Beach and Crescent Beach, and then kick back and relax poolside at one of the accommodations in Shelter Island Heights that guests like for their pools.
What are some accommodations with pools in Shelter Island Heights?
The Chequit: Offers a snack bar/deli, a seasonal outdoor pool, and daily. Shelter Island House: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Features a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Offers sun loungers, an indoor pool, and complimentary wireless internet access.
How many pool hotels will I find in Shelter Island Heights?
Expedia has 10 hotels in Shelter Island Heights for your poolside break.
What is there to see and do in Shelter Island Heights?
Spend some time experiencing the great outdoors at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Country Club, Sylvester Manor, and Menhadden Lane Beach during your stay. Take in the natural beauty of Shelter Island Heights with the island views and beaches.
When is the best time to book a hotel with a pool in Shelter Island Heights?
You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Shelter Island Heights in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.