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
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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$6,368
NT$7,276 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A rectangular swimming pool with a deck area, surrounded by lounge chairs and umbrellas.
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.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

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$8,231
NT$10,307 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn
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 spacious room with wicker furniture, large windows, and a view of the sea.
A seaside restaurant with outdoor seating, a deck, and a view of the ocean.

3. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
NT$8,406
NT$10,508 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A hotel room with a large bed, a sofa, a TV on a shelf, and a window with curtains.
A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.
A bathroom with a shower, a bathtub, a window with a view of trees, a framed picture on the wall, and a potted plant.

4. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
NT$9,920
NT$11,334 total
includes taxes & fees
Sep 15 - Sep 16
West Neck Guesthouse
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.
A deck with outdoor seating, overlooking a body of water with a sunset view.

5. 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$16,042
NT$20,161 total
includes taxes & fees
Sep 14 - Sep 15
The Pridwin Hotel
A poolside area with a hat and towel on a lounge chair.
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.
A modern house with a deck, outdoor seating, and a fire pit.

6. North Fork Resort

North Fork Resort
Greenport
NT$10,167
NT$11,616 total
includes taxes & fees
Sep 14 - Sep 15
North Fork Resort

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$9,143
NT$13,266 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

8. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NT$10,886
NT$13,715 total
includes taxes & fees
Oct 5 - Oct 6
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 hotel lobby with a sofa, chairs, tables, and a large window.

9. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
NT$10,253
NT$11,714 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn
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

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"perfect place"
Joseph 2-night trip
Posted 2 hours ago
Ocean Surf Resort
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 2 hours ago
Faraway Sag Harbor
Kenny's Tipperary Inn

Kenny's Tipperary Inn

10/10 Excellent
"Very clean. Friendly and helpful staff."
Jaroslaw 1-night trip
Posted 2 hours ago
Kenny's Tipperary Inn
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Gorgeous Inn. Excellent experience overall. Need less puffy pillows on beds…bring your own! All 6 adults in our party were uncomfortable with pillows and slept poorly. Celebrating my husband’s 70th and I checked in earlier with staff to be sure they had the cake (as requested I do) and asked if we could have a particular table (or have a choice). We had 6 adults and one high chair. We were told they only had one table that would accommodate our “large” group. The table we were given was just okay…meanwhile there were groups our size and larger being accommodated at other tables. I was really disappointed about that. One final note…it would be nice to have different menus at the bar vs restaurant. Also if you’re staying out of season and plan to use the indoor pool, the room is extremely hot and humid and barely tolerable due to the chemicals. Otherwise staff was delightful, rooms and common areas beautiful!"
Donna 2-night trip
Posted 3 hours ago
Saybrook Point Resort & Marina
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."
Michael 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"I love how its very close to the beach and grocery stores."
Leona 2-night trip
Posted 2 days ago
Ocean Resort Inn
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"This property is a lovely option if you want to be near to central Southampton but not in the middle of it. the room was really nicely appointed, they have a lovely grounds area near the pool, and a really nice pool deck with a pretty big heated pool. We really enjoyed the pool. Only negative is that It's located on a 2 lane highway without much close buy in the way of restaurants or other necessities; getting around was awkward and costly without a car. However, the place we stayed at was nice!"
Nancy 2-night trip
Posted 2 days ago
The Atlantic Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Everything went smoother than I thought it would. The staff couldn’t have been kinder, helpful, or more knowledgeable. The spa treatments and massages were off the charts! We’re looking forward to our next stay and many more to come!"
George 2-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Sound View Greenport: Features a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Atlantic Hotel: Resort, 13-minute walk from The Hamptons Beaches. Features 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. Offers a sauna, a seasonal outdoor pool, and free self parking. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and flat-screen televisions.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Mashomack Preserve. Discover sights such as Shelter Island Historical Society, Crescent Beach, and Gardiner's Bay Country Club 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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