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Hotels with Swimming Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Swimming Pool

Tonight
Aug 6 - Aug 7
Tomorrow
Aug 7 - Aug 8
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Shelter Island Hotels with Swimming Pool

Clinton Motel
Situated in a landscaped area, this single-story building offers a convenient parking space.

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (261)
"For the money this reservation was a real win Clean lovely pool area convenient to everything"
The price is P4,554
P5,237 total
includes taxes & fees
Sep 1 - Sep 2
Clinton Motel
Greenporter Hotel
Relax by the fire pit surrounded by comfortable seating and a serene pool view.

Greenporter Hotel

2.0 star property
9.4 out of 10, Exceptional, (158)
"Great place "
Greenporter Hotel
Quality Inn Old Saybrook - Westbrook
Relax by the oval-shaped pool surrounded by lounge chairs and a high ceiling with a grid-like pattern.

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1008)
"Nice place to rest."
The price is P6,339
P7,290 total
includes taxes & fees
Aug 13 - Aug 14
Quality Inn Old Saybrook - Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook
Surrounded by lush greenery, a serene pond with a central fountain offers a peaceful escape.

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (442)
"Definitely an older property, but staff were helpful people and our room was clean and quiet. Easy car ride to get to the ocean."
The price is P4,620
P5,313 total
includes taxes & fees
Aug 14 - Aug 15
Econo Lodge Inn & Suites Old Saybrook Westbrook
Breakers Montauk
Situated in a grassy area, this charming cottage features a central front door, flanked by two windows with shutters, and a small porch with a bench and umbrella.

Breakers Montauk

3.0 star property
8.4 out of 10, Very Good, (155)
"Wonderful, well kept place. Convenient to the ocean. The pool is nice and it was great having a restaurant on site!"
The price is P10,959
P14,400 total
includes taxes & fees
Sep 1 - Sep 2
Breakers Montauk
The Bentley Hotel Southampton
Relax by the pool surrounded by a scenic view and lounge in style on the tiled deck.

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (303)
"Great place!"
The price is P12,683
P16,135 total
includes taxes & fees
Sep 3 - Sep 4
The Bentley Hotel Southampton
Ocean Vista Resort
Guests can enjoy access to the beach and scenic ocean views.

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (184)
"It waa great for traveling with kids. Close to the beach and my kids loved the indoor pool!"
Ocean Vista Resort
Harborside Motel
Enjoy waterfront views and access to a marina from this coastal property, featuring a swimming pool and lush surroundings.

Harborside Motel

2.5 star property
8.8 out of 10, Excellent, (110)
"I booked last minute and the owner could not have been nicer. She was lovely and the room was immaculate. "
The price is P11,186
P12,781 total
includes taxes & fees
Sep 1 - Sep 2
Harborside Motel
Hampton's Vacation Inn
Relax by the pool with lounge chairs and a shaded seating area nearby.

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (294)
"Great place highly recommended. Quiet and cozy atmosphere. Pool, tennis court, volleyball court and onsite parking made the stay that much better. Amazing staff and super professional. "
The price is P12,971
P14,819 total
includes taxes & fees
Aug 7 - Aug 8
Hampton's Vacation Inn
Ocean Resort Inn
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Ocean Resort Inn

2.0 star property
9.6 out of 10, Exceptional, (436)
"We will return here its a great Location "
The price is P13,202
P16,022 total
includes taxes & fees
Sep 1 - Sep 2
Ocean Resort Inn
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.

Top Shelter Island Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread to the pool area. July is expensive but it was definitely worth it. We live on Long Island and didn't have to deal with flying issues. Just a 2 hour drive and 4 days of relaxing sun....."
Brian 3-night trip
Posted 17 hours ago
Sound View Greenport

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Marram: Hotel, 6-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. Quality Inn Old Saybrook - Westbrook: Offers buffet, an indoor pool, and free self parking. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor pools, a children's pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Whale's Tail, Gardiner's Bay Country Club, and Shelter Island Historical Society during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging 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 38°F.