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

Shelter Island Hotels with Swimming Pool

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Check availability on Shelter Island Hotels with Swimming Pools

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Shelter Island hotels with a pool

Property amenity
Front of property – evening/night
Terrace/patio
Bar (on property)

1. 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.
RM821
RM938 total
includes taxes & fees
28 Oct - 29 Oct
Shelter Island House
A swimming pool with a wooden deck, lounge chairs, and a fence.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
RM731
RM951 total
includes taxes & fees
9 Nov - 10 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A wooden cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
RM918
RM1,157 total
includes taxes & fees
28 Oct - 29 Oct
Oyster Estate
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 beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with large windows, a deck, and a view of the sea at sunset.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
RM731
RM952 total
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A hotel lobby with a sofa, chairs, tables, and a large window.
A waterfront property with a large house, multiple boats docked, and lush greenery.

5. 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.
RM894
RM1,021 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
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 modern living room with a sofa, a dining table, and a kitchen area in the background.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

6. North Fork Resort

North Fork Resort
Greenport
RM1,311
RM1,498 total
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
Outdoor pool
Terrace/patio
Room
Room

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
RM690
RM1,241 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A spacious living room with a fireplace, comfortable seating, and large windows.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
RM1,506
RM1,893 total
includes taxes & fees
16 Nov - 17 Nov
Faraway Sag Harbor
A swimming pool with two lounge chairs and a green umbrella.
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.
A wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.
A wooden building with a white window and a balcony.

9. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
RM819
RM1,099 total
includes taxes & fees
15 Nov - 16 Nov
The Sagaponack
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A living room with a fireplace, two sofas, a coffee table, and a chair.
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

10. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.
RM1,010
RM1,270 total
includes taxes & fees
3 Nov - 4 Nov
Journey East Hampton
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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"This is actually a really great place to stay if you want something reasonable in the Hamptons. The rooms are clean and spacious and the grounds of the hotel are beautiful. I highly recommend!!!"
Constantine 1-night trip
Posted 14 hours ago
The Atlantic Hotel
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Everything was wonderful…location, view, amenities made our stay so memorable. Can’t wait to go back!"
SUZANNE 3-night trip
Posted 2 days ago
Beachcomber Resort at Montauk
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 3 days ago
Sound View Greenport
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Only thing I would say is the TV in the room. Every channel was blurry and you couldn’t really see anything."
saymon 2-night trip
Posted 4 days ago
Quality Inn Old Saybrook - Westbrook
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 12 days ago
Ocean Surf Resort

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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