A pebbled beach with a sunset and a distant bridge.

Hotels with Swimming Pool in Shelter Island Heights, New York

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Check availability on Shelter Island Heights Hotels with Swimming Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Shelter Island Heights hotels with a pool

Property amenity
Terrace/patio
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.
P12,595
P14,389 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.
A backyard with a large chessboard, outdoor furniture, and a house.
A hotel room with a large bed, a sofa, a TV on a shelf, and a window with curtains.

2. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
West Neck Guesthouse
Pool
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

3. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
P10,094
P13,321 total
includes taxes & fees
Nov 1 - Nov 2
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 cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.

4. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
P16,291
P20,525 total
includes taxes & fees
Nov 1 - Nov 2
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 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.

5. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
P14,425
P18,270 total
includes taxes & fees
Nov 1 - Nov 2
Sound View Greenport
Outdoor pool
Beach
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.
P10,591
P19,051 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
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 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.

7. North Fork Resort

North Fork Resort
Greenport
P16,672
P19,048 total
includes taxes & fees
Oct 5 - Oct 6
North Fork Resort
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 spacious hallway with a fireplace, a large window, and a built-in shelving unit.

8. 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.
P13,722
P15,677 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
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.

9. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
P26,222
P32,954 total
includes taxes & fees
Nov 1 - Nov 2
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 marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

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.
P9,336
P10,666 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Long Island East End
View all properties

Choose what matters most at hotels with a pool in Shelter Island Heights

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shelter Island Heights Hotel Reviews

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"it was a good experience."
Jinwoo 1-night trip
Posted 1 day ago
Montauk Yacht Club
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"The beach was perfect"
Igor 1-night trip
Posted 1 day ago
Ocean Vista Resort
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"I felt very comfortable and at ease. I had planned on getting a massage, but never made it. Next time I will book one. The beds were comfortable. The food was good, I enjoyed myself."
LOUISE 2-night trip
Posted 2 days ago
Water's Edge Resort & Spa

Frequently asked questions

What's it like visiting Shelter Island Heights?
If lounging by a pool is your idea of a great vacation, you may want to check out Shelter Island Heights, which has 10 places to stay with pools. While you're visiting, you can explore sights such as Sunset Beach and Crescent Beach, and then kick back and relax poolside at one of the accommodations in Shelter Island Heights that guests like for their pools.
What are some accommodations with pools in Shelter Island Heights?
The Chequit: Offers a private beach, a seasonal outdoor pool, and a full-service spa. The Pridwin Hotel: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool, and free self parking. Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Offshore Montauk: Offers a private beach, a seasonal outdoor pool, and 2 bars.
How many pool hotels will I find in Shelter Island Heights?
Expedia has 10 hotels in Shelter Island Heights for your poolside break.
What is there to see and do in Shelter Island Heights?
Spend some time experiencing the great outdoors at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Country Club, Sylvester Manor, and Menhadden Lane Beach during your stay. Take in the natural beauty of Shelter Island Heights with the island views and beaches.
When is the best time to book a hotel with a pool in Shelter Island Heights?
You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Shelter Island Heights in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.

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