TOP Hotels with Swimming Pool in Shelter Island Heights, NY for 2026

Q: What are some accommodation options with pools in Shelter Island Heights?

The Pridwin Hotel : Features a private beach, a seasonal outdoor pool and a full-service spa. Pier Blue Inn Old Saybrook - Essex : Resort, 13-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool and a private beach. Gurney's Montauk Resort & Seawater Spa : Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach. Montauk Yacht Club : Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport : Features a seasonal outdoor pool, an indoor pool and a private beach.

A pebbled beach with a sunset and a distant bridge.

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Our top choices for Shelter Island Heights hotels with a pool

Shelter Island House

Shelter Island Heights

Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.

₹34,892 total

includes taxes & fees

13 Aug - 14 Aug

West Neck Guesthouse

Shelter Island Heights

Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.

₹34,589 total

includes taxes & fees

27 Jul - 28 Jul

Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

Shelter Island Heights

Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.

₹67,691 total

includes taxes & fees

27 Jul - 28 Jul

Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio

The Harbor Front Inn

Greenport

Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.

₹45,504 total

includes taxes & fees

29 Jul - 30 Jul

Sound View Greenport

Greenport

Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.

₹43,369 total

includes taxes & fees

10 Aug - 11 Aug

North Fork Resort

Greenport

₹43,077 total

includes taxes & fees

27 Jul - 28 Jul

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Cliffside Resort Condominiums

Greenport

Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.

₹35,102 total

includes taxes & fees

29 Jul - 30 Jul

Clinton Motel

Clinton

Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.

₹10,217 total

includes taxes & fees

27 Jul - 28 Jul

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

Breakfast included

4 stars

Top Shelter Island Heights Hotel Reviews

Saybrook Point Resort & Marina

10/10 Excellent

"Everything was great. Loved our room. Only issue was the hot water . It took a long time and never really got hot in the shower."

Montauk Yacht Club

8/10 Good

"It was not user-friendly for handicap people my mother used a Rollator there were stairs everywhere, uneven blocks, etc. you always had to go take steps to your room up or down The serving staff was excellent But be careful of additional charges as I had to really review my folio and was refunded an occurrence They need additional chairs for the pool and bar areas The coffee server at the shop was the only server They need two in the morning"

Frequently asked questions

What's it like visiting Shelter Island Heights?

If taking it easy by the pool is your idea of a great getaway, you may want to consider Shelter Island Heights, which offers 10 places to stay with pools. During your trip, you can explore sights such as Sunset Beach and Crescent Beach, and then relax poolside at one of the accommodation options in Shelter Island Heights that guests like for their pools.

What are some accommodation options with pools in Shelter Island Heights?

The Pridwin Hotel: Features a private beach, a seasonal outdoor pool and a full-service spa. Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach. Montauk Yacht Club: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool and a private beach.

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?

Explore places such as The Hamptons Beaches while you're in the area. Enjoy a stroll along the shore at Sunset Beach and Crescent Beach. 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 that has an outdoor pool if you plan to visit Shelter Island Heights in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 3°C.

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