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
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
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
Bar (on property)
Terrace/patio
Property amenity

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$6,391
NT$7,301 total
includes taxes & fees
Oct 5 - Oct 6
Shelter Island House
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A bathroom with a shower, a bathtub, a window with a view of trees, a framed picture on the wall, and a potted plant.
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.

2. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
NT$9,963
NT$11,383 total
includes taxes & fees
Oct 1 - Oct 2
West Neck Guesthouse
A rectangular swimming pool with a view of the sea, surrounded by lounge chairs and a wooden deck.
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 rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

3. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NT$7,116
NT$9,037 total
includes taxes & fees
Oct 26 - Oct 27
The Harbor Front Inn
A poolside area with sun loungers, a pool, and a building with a balcony.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

4. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NT$8,898
NT$11,211 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A beach bar with wooden chairs and a small table, overlooking 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.
NT$7,866
NT$9,894 total
includes taxes & fees
Oct 6 - Oct 7
Sound View Greenport
Outdoor pool
Terrace/patio
Room
Room

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
NT$7,491
NT$12,082 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums
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.

7. North Fork Resort

North Fork Resort
Greenport
NT$8,460
NT$9,665 total
includes taxes & fees
Sep 30 - Oct 1
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 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.

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.
NT$7,913
NT$9,041 total
includes taxes & fees
Oct 30 - Oct 31
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 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.
NT$13,432
NT$16,881 total
includes taxes & fees
Oct 5 - Oct 6
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.
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.

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.
NT$4,954
NT$5,660 total
includes taxes & fees
Oct 21 - Oct 22
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Front desk helpful! Indoor bar area nice area for single traveler plenty of space."
Toni and Zak 1-night trip
Posted 20 hours ago
Water's Edge Resort & Spa
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Bathroom in my unit was kind of outdated but still adequate Seen another unit and it was updated beautifully"
John 2-night trip
Posted 2 days ago
Ocean Surf Resort
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Great resort for a good price. On the beach."
Thomas 2-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.

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