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
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Shelter Island hotels with a pool

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

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.
₩266,272
₩304,205 total
includes taxes & fees
Oct 25 - Oct 26
Shelter Island House
A swimming pool with a wooden deck, lounge chairs, and a fence.
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.
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.
₩208,387
₩275,864 total
includes taxes & fees
Nov 22 - Nov 23
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
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 wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
₩297,696
₩375,088 total
includes taxes & fees
Oct 25 - Oct 26
Oyster Estate
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A coastal building with a deck extending over the water, featuring large windows and a dining area.
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.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₩229,225
₩299,677 total
includes taxes & fees
Nov 22 - Nov 23
Sound View Greenport
A poolside area with a hat and towel on a lounge chair.
A modern living room with a sofa, a dining table, and a kitchen area in the background.
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.

5. North Fork Resort

North Fork Resort
Greenport
₩425,109
₩485,688 total
includes taxes & fees
Oct 26 - Oct 27
North Fork Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A waterfront property with a large house, multiple boats docked, and lush greenery.

6. 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.
₩289,757
₩331,048 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
Outdoor pool
A balcony with a view of the sea, a dining table, and a blue house in the background.
Beach
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.
₩223,629
₩402,286 total
includes taxes & fees
Nov 15 - Nov 16
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 dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
₩464,404
₩583,637 total
includes taxes & fees
Nov 22 - Nov 23
Faraway Sag Harbor
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.
Beach
A bathtub surrounded by candles and flower petals.

9. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
₩391,767
₩447,588 total
includes taxes & fees
Oct 26 - Oct 27
A Room At The Beach
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.
A balcony with a view of the ocean, a white railing, and two white chairs with blue cushions.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

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.
₩248,873
₩309,027 total
includes taxes & fees
Nov 1 - Nov 2
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

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"The location could not be more perfect! Right on the beach! The rooms are beautiful and spacious. We had to check in late and it could not be easier. We are really looking forward to our next stay here!"
Stefan 1-night trip
Posted 12 hours ago
Ocean Vista Resort
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Always an amazing stay at Gurneys. The ocean views and the restorative spa alone make this place so special. The staff is friendly and the rooms are kept so clean. Highly recommended."
Peter 2-night trip
Posted 21 hours ago
Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
Svetlana 4-night trip
Posted 1 day ago
Montauk Yacht Club
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Great"
allison 3-night trip
Posted 2 days 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 3 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 5 days ago
The Atlantic Hotel

Frequently asked questions

What are some accommodations 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 sun loungers, 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 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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