A wooden gazebo by a pond with a large tree trunk nearby.

Hotels with Swimming Pools in Shelter Island

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Check availability on Shelter Island Hotels with Swimming Pools

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Shelter Island hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

1. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
S$258
includes taxes & fees
3 Nov - 4 Nov
The Harbor Front Inn
Property amenity
Bar (on property)
Property amenity
Terrace/patio

2. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
S$294
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach bar with wooden chairs and a small table, overlooking the sea.
A spacious room with wicker furniture, large windows, and a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.

3. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
S$291
includes taxes & fees
3 Nov - 4 Nov
Sound View Greenport
Outdoor pool
Beach
Terrace/patio
Room

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
S$389
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A poolside area with a hat and towel on a lounge chair.
A modern house with a deck, outdoor seating, and a fire pit.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
A modern bathroom with a black bathtub, white sink, and shower area. There are framed pictures on the wall and a potted plant on the counter.

5. North Fork Resort

North Fork Resort
Greenport
S$363
includes taxes & fees
7 Oct - 8 Oct
North Fork Resort
A poolside area with lounge chairs and yellow umbrellas.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.

6. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
S$419
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

7. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
S$320
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A spacious living room with a fireplace, comfortable seating, and large windows.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
S$658
includes taxes & fees
2 Nov - 3 Nov
Faraway Sag Harbor
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

9. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
S$210
includes taxes & fees
12 Oct - 13 Oct
The Bentley Hotel Southampton
Outdoor pool
Terrace/patio
Living area
Reception

10. East Hampton House Resort

East Hampton House Resort
East Hampton North
  • Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
S$232
includes taxes & fees
2 Nov - 3 Nov
East Hampton House Resort
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The property was definitely worth a five-star rating and the views of the Bay were tremendous! The rooms were very clean and the beds were super comfortable. I had a wonderful breakfast looking out over the water. It was magical"
Melanie 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Such a great spot! Clean, easy access, everything you need!!"
Christian 3-night trip
Posted 2 days ago
Ocean Resort Inn
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beachcomber was wonderful loved it"
elizabeth 3-night trip
Posted 3 days ago
Beachcomber Resort at Montauk
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"it was a good experience."
Jinwoo 1-night trip
Posted 4 days ago
Montauk Yacht Club

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
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. Provides a sauna, a seasonal outdoor pool and free self parking. Offshore Montauk: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Features sunloungers, an indoor pool and complimentary wireless Internet access.
What is there to see and do in Shelter Island?
Surround yourself with nature at Mashomack Preserve and Sunset Beach. Discover sights such as Shelter Island Historical Society, Wades Beach and Crescent Beach 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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