Hotels with Swimming Pool in Shelter Island Heights, New York

  • 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 Heights Hotels with Swimming Pool

Our top choices for Shelter Island Heights hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The Pridwin Hotel
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very Good, (37 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
West Neck Guesthouse
Property amenity

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (57 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
Shelter Island House
Seasonal outdoor pool, sun loungers

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.
Ocean Resort Inn
Seasonal outdoor 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.
Clinton Motel
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, (473 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
North Fork Resort
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (188 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
Breakers Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers

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.
Marram
Seasonal outdoor pool, sun loungers

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.
Aqualina Inn Montauk
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

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

Breakfast included
4 stars

Top Shelter Island Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

6/10 Okay
"Bedding was suboptimal and toilets clogged. Additionally, very noisy due to 2 weddings in the resort that night… so not very relaxing."
Pascale 1-night trip
Posted 8 hours ago
Water's Edge Resort & Spa

Frequently asked questions

What's it like visiting Shelter Island Heights?
If lounging by a pool is your idea of a great vacation, you may want to check out Shelter Island Heights, which has 10 places to stay with pools. While you're visiting, you can explore sights such as Sunset Beach and Crescent Beach, and then kick back and relax poolside at one of the accommodations in Shelter Island Heights that guests like for their pools.
What are some accommodations with pools in Shelter Island Heights?
The Pridwin Hotel: Features a private beach, a seasonal outdoor pool, and a full-service spa. Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children's pool, and a private beach. The Bentley Hotel Southampton: Offers free self parking, a seasonal outdoor 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 with an outdoor swimming pool if you will be visiting Shelter Island Heights in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.

Explore a world of travel with Expedia