Top 10 Hotels with Pool & Accommodation in Shelter Island from AU$131

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. The Atlantic Hotel : Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Bentley Hotel Southampton : Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Montauk Yacht Club : Hotel, 5-minute walk from The Hamptons Beaches. Offers 2 outdoor swimming pools, a children's pool and a private beach.

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Our top choices for Shelter Island hotels with a pool

Clinton Motel

Clinton

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

includes taxes & fees

11 June - 12 June

Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

Culloden Shores

Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.

includes taxes & fees

11 June - 12 June

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.

includes taxes & fees

21 June - 22 June

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.

includes taxes & fees

25 June - 26 June

Seasonal outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas

Ocean Surf Resort

Downtown Montauk

Seasonal Montauk retreat with sun-drenched pool deck offering ocean views, just steps from city centre.

includes taxes & fees

15 June - 16 June

Breakers Montauk

Montauk

Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.

includes taxes & fees

16 June - 17 June

The Penny Lane

Hampton Bays

Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.

includes taxes & fees

6 July - 7 July

Sun N Sound

Culloden Shores

Splash into refreshing waters at this beach-adjacent retreat with sun-soaked outdoor pool.

includes taxes & fees

11 June - 12 June

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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

Quality Inn Old Saybrook - Westbrook

4/10 Poor

"The place is in dire need of a makeover. In the bathroom... No exhaust fan... Hinges and towel racks are rusted... Wall paper is peeling off the walls... Tub/shower faucet is connected wrong. Hot is cold and Cold is hot... Door has noticeable cracks. The front half of the room had no lights. Until this place get renovated, I will not stay there again."

Hyatt Place Long Island East End

10/10 Excellent

"The property itself was nice, and the breakfast was good with a decent selection of options. However, the cleanliness of the room was disappointing. There was a noticeable layer of dust on the tables, coffee machine, and even the glasses, which gave the impression that the room had not been thoroughly cleaned before my stay. While the hotel has some positive aspects, housekeeping standards need improvement."

Gurney's Montauk Resort & Seawater Spa

6/10 Okay

"Great location, excellent facilities. Staff very mixed - some incredible and some terrible. Cumulative number of issues but dealt with by a member of the management team after getting fed up of a number of things, Including: Dog mess left for > 24 hours after reporting it. Staff member laughed and clearly did nothing after reporting it. Not our dog. Had to call 4 times to get our daughters bed made up in the room. Despite being on the booking months in advance. Asked for an ice cream for our daughter and told i was lying when i said they’d done it for her the two proceeding days and they couldnt get her one. Not the kind of treatment or experience from a resort of this quality."

Kenny's Tipperary Inn

10/10 Excellent

"The property is very nice, quiet, and quaint. We stayed the night to head out on a fishing charter at 4am, and the location is literally walking distance. The room and property are very clean, and being greeted by very friendly staff was great after a long drive. The beds were comfortable, linens crisp and clean. The ceiling in the bath was a bit dated, but did not take away from a very comfortable stay. I booked through Expedia and the rate was the lowest in the area, and well worth the stay. And, beautiful friendly dogs greeted us. If we go back to Montauk, we will definitely check for rooms here first. Highly recommend."

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. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Bentley Hotel Southampton: Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Offers 2 outdoor swimming pools, a children's pool and a private beach.

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, Shelter Island Historical Society and Havens House 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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