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

Search Hotels with Pool in Shelter Island

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Check availability on Shelter Island Hotels with Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Shelter Island hotels with a pool

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

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.
฿6,754
฿7,716 total
includes taxes & fees
6 Oct - 7 Oct
Shelter Island House
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
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 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.
฿5,406
฿7,135 total
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
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.
A wooden cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
฿8,725
฿10,994 total
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A coastal building with large windows, a deck, and a view of the sea at sunset.
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.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
฿6,434
฿8,310 total
includes taxes & fees
2 Nov - 3 Nov
Sound View Greenport
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 hotel lobby with a sofa, chairs, tables, and a large window.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

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.
฿7,349
฿8,397 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
Outdoor pool
Room
Room
Terrace/patio

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
฿5,672
฿10,204 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
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 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.

7. North Fork Resort

North Fork Resort
Greenport
฿8,940
฿10,214 total
includes taxes & fees
7 Oct - 8 Oct
North Fork Resort
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 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.
฿13,742
฿17,271 total
includes taxes & fees
2 Nov - 3 Nov
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
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.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

9. 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.
฿5,235
฿5,981 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Long Island East End
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
A balcony with a view of the ocean, a white railing, and two white chairs with blue cushions.
A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

10. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
  • Pristine waters await at this coastal retreat with private beach access and year-round pools.
฿5,260
฿6,628 total
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa
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

8/10 Good
"My only complaint would be i wish there was a Keurig machine in the room instead of an espresso machine. Would definitely stay there again."
Fred 2-night trip
Posted 1 hour ago
The Atlantic Hotel
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Montauk Yacht Club was the perfect getaway for my boyfriend and I to celebrate our 3 year anniversary. Our room was spotless and had a great view of the water. We did mention to them ahead of time that it was our anniversary, thinking they might have some champagne or something waiting in the room for us, but they did not. Nonetheless, it was still a perfect stay. We played tennis and the courts were beautiful. The on-site restaurant was very yummy as well! I definitely recommend coming during the off season, as it is way less crowded in town and very relaxing."
Sarah 3-night trip
Posted 17 hours ago
Montauk Yacht Club
Sun N Sound

Sun N Sound

8/10 Good
"Everything was fine accept there really wasn’t any privacy people and staff were always by room and outdoor space"
Joseph 2-night trip
Posted 17 hours ago
Sun N Sound
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 22 hours ago
Ocean Surf Resort
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 3 days 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 4 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 5 days ago
Beachcomber Resort at Montauk

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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