A pebbled beach with a sunset and a distant bridge.

Search Hotels with Pool in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Pool

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Shelter Island Heights 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.
Rp3.602.979
Rp4.116.258 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
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 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.

2. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
Rp5.612.591
Rp6.412.497 total
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse
A swimming pool with lounge chairs and a wooden deck.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
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.

3. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
Rp4.012.062
Rp5.095.092 total
includes taxes & fees
25 Oct - 26 Oct
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 beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
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.
Rp4.480.225
Rp5.629.966 total
includes taxes & fees
25 Oct - 26 Oct
Sound View Greenport
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 hotel room with two beds, a large window, a ceiling fan, and a painting on the wall.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

5. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
Rp5.657.348
Rp7.127.900 total
includes taxes & fees
5 Oct - 6 Oct
Oyster Estate

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
Rp4.223.497
Rp6.811.554 total
includes taxes & fees
25 Oct - 26 Oct
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 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
Rp4.882.148
Rp5.577.853 total
includes taxes & fees
25 Oct - 26 Oct
North Fork Resort
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

8. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
  • Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
Rp1.917.411
Rp2.205.023 total
includes taxes & fees
4 Oct - 5 Oct
Quality Inn Old Saybrook - Westbrook
A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.
A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.
A multi-story residential building with blue trim and large windows.
A hotel lobby with a reception desk, a flat-screen TV mounted above a fireplace, and comfortable seating areas.

9. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
Old Saybrook
  • Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
Rp1.200.038
Rp1.380.044 total
includes taxes & fees
25 Oct - 26 Oct
Econo Lodge Inn & Suites Old Saybrook Westbrook
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A motel with a large parking lot and multiple rooms.
A parking lot with a building in the background.

10. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
Rp1.396.434
Rp1.605.899 total
includes taxes & fees
27 Sept - 28 Sept
Clinton Motel
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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 Surf Resort

Ocean Surf Resort

8/10 Good
"Beautiful view of the ocean, helpful staff. We will be returning."
Carolyn 3-night trip
Posted 22 hours ago
Ocean Surf Resort
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"We stayed in the ocean front room. The room and view were beautiful. We had dinner at GIGIs. The food was good. The menu selection Was limited for us because we do not eat fish. The negative with Gurneys is the rooms are not connected to the main building. They do provide a car service to pick you up. I feel this limits you. We would have gone down for a drink but it seemed too involved to get there. This resort is not for seniors ."
salvatore 2-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Staff was very friendly room was clean bed was comfortable"
Richard 1-night trip
Posted 2 days ago
Ocean Vista Resort
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"I really love this hotel! The rooms are beautiful, the service is excellent, and I’ve had a great experience every time I’ve stayed there. I’ve been a few times already and will definitely be coming back next year!"
Veronika 2-night trip
Posted 4 days ago
Montauk Yacht Club
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Closest to beach and town"
john 1-night trip
Posted 5 days ago
Ocean Resort Inn

Frequently asked questions

What's it like visiting Shelter Island Heights?
If taking it easy by the pool is your idea of a great getaway, you may want to consider Shelter Island Heights, which offers 10 places to stay with pools. During your trip, you can explore sights such as Sunset Beach and Crescent Beach, and then relax poolside at one of the accommodation options in Shelter Island Heights that guests like for their pools.
What are some accommodation options 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 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
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 that has an outdoor pool if you plan to visit Shelter Island Heights in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 3°C.

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