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Hotels with Pool & Resorts in Shelter Island Heights from AU$136

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Check availability on Shelter Island Heights Hotels with Pool

Our top choices for Shelter Island Heights hotels with a pool

Seasonal outdoor pool, pool umbrellas, pool 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, (878)
"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, (1269)
"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 AU$269
includes taxes & fees
12 Jan - 13 Jan 2026
Montauk Manor
Outdoor pool
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.2 out of 10, Wonderful, (81)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is AU$287
includes taxes & fees
1 Jan - 2 Jan 2026
Offshore Montauk
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is AU$306
includes taxes & fees
23 Dec - 24 Dec
The Harbor Front Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is AU$349
includes taxes & fees
23 Dec - 24 Dec
Sound View Greenport
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is AU$196
includes taxes & fees
21 Dec - 22 Dec
Hyatt Place Long Island East End
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, (398)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is AU$218
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
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, (1005)
"Clean Room/Polite staff/ Breakfast was basic/ pool area looked maintained."
United States
Sara
The price is AU$136
includes taxes & fees
1 Jan - 2 Jan 2026
Sleep Inn & Suites Niantic North
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (443)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is AU$200
includes taxes & fees
25 Dec - 26 Dec
Hamlet Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1004)
"The staff was friendly. The room was good. "
United States
Narida
The price is AU$176
includes taxes & fees
29 Dec - 30 Dec
Quality Inn Old Saybrook - Westbrook
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Everything was perfect. Staff, room, experience. Will definitely stay again. "
Kristy 1-night trip
Posted 4 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What's it like visiting Shelter Island Heights?
If taking it easy by the pool is your idea of a great getaway, you may want to consider Shelter Island Heights, which offers 10 places to stay with pools. During your trip, you can explore sights such as Sunset Beach and Crescent Beach, and then relax poolside at one of the accommodation options in Shelter Island Heights that guests like for their pools.
What are some accommodation options 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 sunloungers, 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 that has an outdoor pool if you plan to visit Shelter Island Heights in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 3°C.