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
  • 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

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (309 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is NT$2,418
NT$2,781 total
includes taxes & fees
May 13 - May 14
Clinton Motel

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is NT$4,241
NT$4,846 total
includes taxes & fees
May 18 - May 19
Ocean Resort Inn

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, (473 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is NT$2,529
NT$2,909 total
includes taxes & fees
May 18 - May 19
Econo Lodge Inn & Suites Old Saybrook Westbrook

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is NT$8,452
NT$9,657 total
includes taxes & fees
May 19 - May 20
The Penny Lane

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
The price is NT$9,328
NT$10,658 total
includes taxes & fees
May 25 - May 26
North Fork Cottages & RV Resort

Sun N Sound

Sun N Sound
2.5 star property
Culloden Shores
9.0 out of 10, Wonderful, (269 reviews)
  • cleanliness
    Splash into refreshing waters at this beach-adjacent retreat with sun-soaked outdoor pool.
The price is NT$3,209
NT$4,178 total
includes taxes & fees
May 20 - May 21
Sun N Sound

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
The price is NT$5,331
NT$12,370 total
includes taxes & fees
May 14 - May 15
Marram

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (496 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is NT$4,241
NT$4,846 total
includes taxes & fees
May 20 - May 21
Aqualina Inn Montauk

Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
The price is NT$7,126
NT$11,730 total
includes taxes & fees
May 26 - May 27
Offshore Montauk

Ocean Surf Resort

Ocean Surf Resort
2.0 star property
Downtown Montauk
8.4 out of 10, Very Good, (239 reviews)
  • cleanliness
    Seasonal Montauk retreat with sun-drenched pool deck offering ocean views, just steps from downtown.
The price is NT$8,135
NT$9,294 total
includes taxes & fees
May 17 - May 18
Ocean Surf 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.

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

Top Shelter Island Hotel Reviews

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. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor pools, a children's pool, and a private beach. The Bentley Hotel Southampton: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex: Features 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 Crescent Beach. Discover sights such as Gardiner's Bay Country Club, Mashomack Preserve, 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.

Explore a world of travel with Expedia