🏊 Top 10 Shelter Island Hotels with Swimming Pool

Q: 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.

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Our top choices for Shelter Island hotels with a pool

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Old Saybrook

Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.

RM420 total

includes taxes & fees

29 Mar - 30 Mar

Clinton Motel

Clinton

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

RM353 total

includes taxes & fees

23 Mar - 24 Mar

Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.

RM304 total

includes taxes & fees

5 Apr - 6 Apr

Water's Edge Resort & Spa

Westbrook Center

Pristine waters await at this coastal retreat with private beach access and year-round pools.

RM953 total

includes taxes & fees

23 Mar - 24 Mar

The Hampton Maid

Hampton Bays

Splash into summer at this Hampton motel, where the seasonal pool and massage services await.

Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

The Harbor Front Inn

Greenport

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

RM756 total

includes taxes & fees

24 Mar - 25 Mar

Hyatt Place Long Island East End

Riverhead

Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.

RM507 total

includes taxes & fees

29 Mar - 30 Mar

Beach Plum Resort

Montauk

Outdoor pool paradise offers relaxation and sunshine after coastal adventures.

RM910 total

includes taxes & fees

1 Apr - 2 Apr

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

Breakfast included

4 stars

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

10/10 Excellent

"Staff was amazing and helpful. The rooms were lovely and the beds so comfortable."

Gurney's Montauk Resort & Seawater Spa

8/10 Good

"The food was delicious. There was an issue with the pool which will be fixed soon. My big complaint was room location. I am a senior citizen and my room was in the 700's. Many steep stairs to get down to main building. They offered a ride from my room to main building which I had to use because it was just too far to walk in the dark alone. Walking up to my room was not an option. This may be find for a young family but not for me."

Saybrook Point Resort & Marina

10/10 Excellent

"Our group of 6 girlfriends had an amazing stay at Saybrook Point Resort & Marina. From the moment we arrived, we knew the weekend was going to be very special. The staff was always warm & welcoming. Shoutout to Scott at reception for ensuring a perfect stay! Dinner at Fresh Salt was delicious & the atmosphere was lively. Shuttle into town was a great option. Can’t wait to book another visit!"

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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Check availability on Shelter Island Hotels with Swimming Pools

Our top choices for Shelter Island hotels with a pool

Quality Inn Old Saybrook - Westbrook

Clinton Motel

Econo Lodge Inn & Suites Old Saybrook Westbrook

Water's Edge Resort & Spa

The Hampton Maid

The Harbor Front Inn

Hyatt Place Long Island East End

Beach Plum Resort

Sag Harbor Inn

The Bentley Hotel Southampton

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

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Sound View Greenport

Gurney's Montauk Resort & Seawater Spa

Saybrook Point Resort & Marina

Quality Inn Old Saybrook - Westbrook

Hyatt Place Long Island East End

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