The Best Hotels with a Pool in Shelter Island Heights, NY from ₩154,362 in 2026

Q: 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. 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 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.

₩527,166 total

includes taxes & fees

Aug 13 - Aug 14

West Neck Guesthouse

Shelter Island Heights

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

₩522,585 total

includes taxes & fees

Aug 4 - Aug 5

Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

Shelter Island Heights

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

₩1,135,911 total

includes taxes & fees

Aug 24 - Aug 25

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

The Harbor Front Inn

Greenport

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

₩772,497 total

includes taxes & fees

Aug 11 - Aug 12

Sound View Greenport

Greenport

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

₩761,177 total

includes taxes & fees

Aug 11 - Aug 12

North Fork Resort

Greenport

₩880,628 total

includes taxes & fees

Aug 2 - Aug 3

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.

₩761,269 total

includes taxes & fees

Jul 30 - Jul 31

Clinton Motel

Clinton

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

₩154,362 total

includes taxes & fees

Jul 27 - Jul 28

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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

Hampton's Vacation Inn

10/10 Excellent

"Excellent!! Would stay again in a heartbeat!"

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 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. 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 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 like 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 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.

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