Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
  • cleanliness
    Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.
The price is ₩213,869
₩285,084 total
includes taxes & fees
Mar 17 - Mar 18
Windward Shores Ocean Resort
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is ₩138,818
₩159,640 total
includes taxes & fees
Mar 22 - Mar 23
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (303 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is ₩116,868
₩134,398 total
includes taxes & fees
Mar 24 - Mar 25
Clinton Motel
Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (115 reviews)
The price is ₩229,377
₩347,655 total
includes taxes & fees
Mar 29 - Mar 30
Offshore Montauk
Individually decorated, individually furnished, desk, laptop workspace

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, (468 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is ₩100,432
₩115,497 total
includes taxes & fees
Mar 22 - Mar 23
Econo Lodge Inn & Suites 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, (458 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
The price is ₩146,984
₩189,985 total
includes taxes & fees
Mar 17 - Mar 18
Hamlet Inn
Front of property

Beach Plum Resort

Beach Plum Resort
3.0 star property
Montauk
9.0 out of 10, Wonderful, (159 reviews)
  • cleanliness
    Outdoor pool paradise offers relaxation and sunshine after coastal adventures.
The price is ₩274,640
₩346,364 total
includes taxes & fees
Apr 1 - Apr 2
Beach Plum Resort
Exterior

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,304 reviews)
  • cleanliness
    Refreshing hilltop retreat with year-round pool access and sweeping ocean vistas.
The price is ₩173,055
₩227,039 total
includes taxes & fees
Mar 19 - Mar 20
Montauk Manor
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, (574 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is ₩200,923
₩272,346 total
includes taxes & fees
Mar 22 - Mar 23
The Harbor Front Inn
Property map

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
The price is ₩355,999
₩406,728 total
includes taxes & fees
Apr 1 - Apr 2
North Fork Cottages & RV Resort
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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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful location, nicely appointed rooms, lovely staff. Food got mixed reviews from our group. Fantastic venue for bridal shower. "
Kathryn 2-night trip
Posted 5 hours ago
Water's Edge Resort & Spa

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Water's Edge Resort & Spa: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Blue Hotel: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and flat-screen televisions. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars.
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 Shell Beach 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.