A pebbled beach with a sunset and a distant bridge.

Find Hotels with a Pool in Shelter Island Heights, NY

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Check availability on Shelter Island Heights Hotels with a Pool

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

Our top choices for Shelter Island Heights 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.
AED 739
AED 844 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
Pool
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.
AED 556
AED 740 total
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
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 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.
AED 955
AED 1,203 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 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.
AED 786
AED 1,003 total
includes taxes & fees
1 Nov - 2 Nov
Sound View Greenport
Outdoor pool
Room
Beach
Terrace/patio

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
AED 621
AED 1,117 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
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 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.

6. North Fork Resort

North Fork Resort
Greenport
AED 913
AED 1,043 total
includes taxes & fees
7 Oct - 8 Oct
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 hallway with a fireplace, a large window, and a built-in shelving unit.
A waterfront property with a large house, multiple boats docked, and lush greenery.

7. 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.
AED 804
AED 919 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
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 spacious living room with a fireplace, comfortable seating, and large windows.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
AED 1,537
AED 1,932 total
includes taxes & fees
1 Nov - 2 Nov
Faraway Sag Harbor
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.
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.

9. 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.
AED 576
AED 725 total
includes taxes & fees
4 Oct - 5 Oct
Water's Edge Resort & Spa
An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.
A two-story Victorian-style house with a balcony, a porch, and a small tower.
A marina at sunset with boats docked, a fire feature on the deck, and a chair.
A marina with boats docked, a fire pit table, and outdoor seating.

10. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center
  • Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
AED 1,062
AED 1,349 total
includes taxes & fees
1 Nov - 2 Nov
Saybrook Point Resort & Marina
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

Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Right by the water and walking distance to all restaurants and town! Great experience."
Samantha 2-night trip
Posted 2 hours 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 22 hours ago
Beachcomber Resort at Montauk
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"it was a good experience."
Jinwoo 1-night trip
Posted 2 days ago
Montauk Yacht Club
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"The beach was perfect"
Igor 1-night trip
Posted 2 days ago
Ocean Vista Resort

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.