Find Hotels with a Pool in Shelter Island, NY

  • 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

Our top choices for Shelter Island hotels with a pool

Exterior

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,281 reviews)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
The price is ₩204,242
₩262,184 total
includes taxes & fees
Jan 19 - Jan 20
Montauk Manor
Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (93 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is ₩171,086
₩279,647 total
includes taxes & fees
Feb 1 - Feb 2
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (882 reviews)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

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 ₩174,107
₩241,003 total
includes taxes & fees
Jan 19 - Jan 20
The Harbor Front Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (606 reviews)
"Nice place"
United States
Mateusz
The price is ₩197,655
₩267,916 total
includes taxes & fees
Jan 21 - Jan 22
Sound View Greenport
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is ₩131,520
₩151,248 total
includes taxes & fees
Feb 15 - Feb 16
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

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 ₩128,646
₩166,282 total
includes taxes & fees
Jan 19 - Jan 20
Hamlet Inn
Exterior

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (298 reviews)
"Very clean room, nice staff. Will definitely come back . "
United States
Kosuke
Daunt's Albatross Motel
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (300 reviews)
"Is good"
United States
Miguel
The price is ₩111,994
₩128,793 total
includes taxes & fees
Jan 19 - Jan 20
Clinton Motel
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (425 reviews)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is ₩178,493
₩205,402 total
includes taxes & fees
Jan 29 - Jan 30
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.
View all properties

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible ! "
Etsuko 2-night trip
Posted 6 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are some accommodations 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 sun loungers, 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 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.