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

Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
Aug 19 - Aug 20
Tomorrow
Aug 20 - Aug 21
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Shelter Island hotels with a pool

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.
NT$10,105
NT$11,546 total
includes taxes & fees
Sep 2 - Sep 3
Shelter Island House
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 balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NT$8,828
NT$11,728 total
includes taxes & fees
Sep 8 - Sep 9
The Harbor Front Inn
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A bathroom with a shower, a bathtub, a window with a view of trees, a framed picture on the wall, and a potted plant.
A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.
A hotel room with a large bed, a sofa, a TV on a shelf, and a window with curtains.

3. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
NT$10,018
NT$11,445 total
includes taxes & fees
Sep 2 - Sep 3
West Neck Guesthouse
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
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.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
NT$8,665
NT$12,638 total
includes taxes & fees
Sep 15 - Sep 16
Sound View Greenport
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.

5. North Fork Resort

North Fork Resort
Greenport
NT$10,267
NT$11,730 total
includes taxes & fees
Sep 7 - Sep 8
North Fork Resort
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A deck with outdoor seating, overlooking a body of water with a sunset view.
A person sitting on a bench with a drink, overlooking a waterfront with a flag and a view of the water.

6. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
NT$17,073
NT$21,456 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
NT$9,794
NT$14,038 total
includes taxes & fees
Sep 7 - Sep 8
Cliffside Resort Condominiums
A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.
A cozy interior with a wooden bench, a sofa, and a bar area.
A cozy interior with a bar area, seating, and a fireplace.
A spacious room with a wooden bar area, shelves with books and decorative items, a patterned wall, and a large window.

8. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NT$10,401
NT$13,105 total
includes taxes & fees
Sep 7 - Sep 8
Oyster Estate
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.
A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

9. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
  • Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
NT$3,232
NT$3,717 total
includes taxes & fees
Sep 13 - Sep 14
Quality Inn Old Saybrook - Westbrook
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

8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Debra 1-night trip
Posted 7 hours ago
Water's Edge Resort & Spa
Kenny's Tipperary Inn

Kenny's Tipperary Inn

10/10 Excellent
"Very clean rooms and pet friendly! Good location"
Tiara 3-night trip
Posted 1 day ago
Kenny's Tipperary Inn
Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Theresa 4-night trip
Posted 1 day ago
Hampton's Vacation Inn
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Hotel very well situated with a nice beach and a great pool. The rooms were clean and spacious. There were a lot of families so we couldn’t just sit and enjoy the view with toddlers running around - but that was me 20 years ago. I would recommend but next time I would want to book the private patio rooms. Continental breakfast was great - all around fantastic stay."
Karen 2-night trip
Posted 1 day ago
Sound View Greenport
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"It was a great stay!"
Tynan 2-night trip
Posted 2 days ago
Ocean Resort Inn

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool, and free self parking. Offshore Montauk: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Atlantic Hotel: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor 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 Mashomack Preserve, 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.

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