A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights Hotel Guide - Hotels with Pool in Shelter Island Heights, New York

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Check availability on Shelter Island Heights Hotels with Pool

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Shelter Island Heights hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A deck with outdoor seating, overlooking a body of water with a sunset view.
A person sitting on a bench with a drink, overlooking a waterfront with a flag and a view of the water.

1. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
€575
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel

2. 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.
€309
includes taxes & fees
31 Aug - 1 Sept
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.

3. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
€307
includes taxes & fees
1 Sept - 2 Sept
West Neck Guesthouse
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.

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
€314
includes taxes & fees
8 Sept - 9 Sept
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 spacious room with wicker furniture, large windows, and a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

5. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
€339
includes taxes & fees
15 Sept - 16 Sept
Sound View Greenport
A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.
A cozy interior with a wooden bench, a sofa, and a bar area.
A bedroom with a bed, bedside tables, a nightstand, a lamp, a painting, a robe, and a bathroom door.
A cozy interior with a bar area, seating, and a fireplace.

6. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
€351
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate
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 house with a deck, outdoor seating, and a fire pit.
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
€314
includes taxes & fees
9 Sept - 10 Sept
North Fork Resort

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
€376
includes taxes & fees
7 Sept - 8 Sept
Cliffside Resort Condominiums
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

9. 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.
€100
includes taxes & fees
13 Sept - 14 Sept
Quality Inn 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 a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
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.
€78
includes taxes & fees
2 Sept - 3 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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"I liked the property. It was nice. The spa was sort of interesting. My boyfriend gets a little sea sick on boats"
David 5-night trip
Posted less than an hour ago
Montauk Yacht Club
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The views are amazing! The breakfast was a great perk. Short drive to town but you really don't need to leave the grounds with bar/restaurant/beach/pool all there."
Catherine 2-night trip
Posted 1 day ago
Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Debra 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa
Kenny's Tipperary Inn

Kenny's Tipperary Inn

10/10 Excellent
"Very clean rooms and pet friendly! Good location"
Tiara 3-night trip
Posted 3 days ago
Kenny's Tipperary 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 Pridwin Hotel: Features a private beach, a seasonal outdoor pool and a full-service spa. The Chequit: Provides free self parking, a seasonal outdoor pool and complimentary bicycles. West Neck Guesthouse: Offers a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Offers a seasonal outdoor pool, an indoor pool and a private beach.
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.