Shelter Island Hotels with Swimming Pool

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Our top choices for Shelter Island hotels with a pool

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is RM365
RM420 total
includes taxes & fees
29 Mar - 30 Mar
Quality Inn Old Saybrook - Westbrook

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (304 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is RM307
RM353 total
includes taxes & fees
23 Mar - 24 Mar
Clinton Motel

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, (469 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is RM264
RM304 total
includes taxes & fees
5 Apr - 6 Apr
Econo Lodge Inn & Suites Old Saybrook Westbrook

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Pristine waters await at this coastal retreat with private beach access and year-round pools.
The price is RM769
RM953 total
includes taxes & fees
23 Mar - 24 Mar
Water's Edge Resort & Spa

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (689 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
The Hampton Maid

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (576 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is RM563
RM756 total
includes taxes & fees
24 Mar - 25 Mar
The Harbor Front Inn

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
The price is RM444
RM507 total
includes taxes & fees
29 Mar - 30 Mar
Hyatt Place Long Island East End

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 RM722
RM910 total
includes taxes & fees
1 Apr - 2 Apr
Beach Plum Resort

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (585 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
The price is RM807
RM922 total
includes taxes & fees
23 Mar - 24 Mar
Sag Harbor Inn

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (450 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is RM516
RM593 total
includes taxes & fees
5 Apr - 6 Apr
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.

Choose what matters most at hotels with a pool in Shelter Island

Top Shelter Island Hotel Reviews

Frequently asked questions

What are some accommodation options 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 sunloungers, 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 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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