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

Search Hotels with Swimming Pool in Shelter Island

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Check availability on Shelter Island Hotels with Swimming Pool

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Shelter Island hotels with a pool

Property amenity
Front of property – evening/night
Property amenity
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.
₹19,084
₹21,802 total
includes taxes & fees
25 Oct - 26 Oct
Shelter Island House
A swimming pool with a wooden deck, lounge chairs, and a fence.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A bar area with wooden bar stools and a bookshelf.
A hotel room with a bed, a chair, and a balcony with a view of greenery.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₹13,890
₹18,577 total
includes taxes & fees
22 Nov - 23 Nov
The Harbor Front Inn
A poolside area with sun loungers, a pool, and a building with a balcony.
A cozy interior with a bar area, seating, and a fireplace.
A bedroom with a large bed, a window with curtains, a wall-mounted lamp, and a framed artwork.
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.
₹20,614
₹25,972 total
includes taxes & fees
23 Nov - 24 Nov
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 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.
₹15,279
₹20,164 total
includes taxes & fees
22 Nov - 23 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.
₹20,689
₹23,637 total
includes taxes & fees
2 Nov - 3 Nov
Sag Harbor Inn
A poolside area with a hat and towel on a lounge chair.
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.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
A modern living room with a sofa, a dining table, and a kitchen area in the background.

6. North Fork Resort

North Fork Resort
Greenport
₹28,667
₹32,752 total
includes taxes & fees
28 Oct - 29 Oct
North Fork Resort
Outdoor pool
Room
A balcony with a view of the sea, a dining table, and a blue house in the background.
Terrace/patio

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₹16,028
₹28,832 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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
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.
₹31,620
₹39,738 total
includes taxes & fees
23 Nov - 24 Nov
Faraway Sag Harbor
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A modern hotel room with a bed, bedside table, and a view of the garden.
A bar area with shelves stocked with various bottles and glasses.

9. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
₹55,545
₹63,791 total
includes taxes & fees
26 Oct - 27 Oct
Topping Rose House
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.
A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

10. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
  • Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
₹13,086
₹14,951 total
includes taxes & fees
3 Nov - 4 Nov
Hyatt Place Long Island East End
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
Svetlana 4-night trip
Posted 4 hours ago
Montauk Yacht Club
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Great"
allison 3-night trip
Posted 1 day ago
Water's Edge Resort & Spa
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"Lovely view of the ocean. Bathroom was fine. Room was updated. Only had one nightstand and lamp."
harriet 2-night trip
Posted 2 days ago
Ocean Surf Resort
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 4 days ago
The Atlantic Hotel

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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