A pebbled beach with a sunset and a distant bridge.

Hotels with Pool & Resorts in Shelter Island Heights from NZ$158

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Check availability on Shelter Island Heights Hotels with Pool

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 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
Front of property – evening/night
Bar (on property)
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.
NZ$406
includes taxes & fees
5 Oct - 6 Oct
Shelter Island House
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
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.
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.
NZ$632
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse
A rectangular swimming pool with a view of the sea, surrounded by lounge chairs and a wooden deck.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
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.

3. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NZ$466
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 spacious room with wicker furniture, large windows, and a view of the sea.
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.
NZ$510
includes taxes & fees
28 Oct - 29 Oct
Sound View Greenport
Outdoor pool
Beach
Terrace/patio
Room

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
NZ$671
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 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.

6. North Fork Resort

North Fork Resort
Greenport
NZ$519
includes taxes & fees
30 Sept - 1 Oct
North Fork Resort
A poolside area with sun loungers, a pool, and a building with a balcony.
A hotel room with two beds, a large window, a ceiling fan, and a painting 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 desk with drawers, a chair, a lamp, and a framed picture on the wall.

7. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NZ$623
includes taxes & fees
5 Oct - 6 Oct
Oyster Estate
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.
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.

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.
NZ$205
includes taxes & fees
30 Oct - 31 Oct
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 motel with a large parking lot and multiple rooms.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A parking lot with a building in the background.

9. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
NZ$158
includes taxes & fees
30 Sept - 1 Oct
Clinton Motel
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

10. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
NZ$298
includes taxes & fees
5 Oct - 6 Oct
The Bentley Hotel Southampton
View all properties

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

Breakfast included
4 stars
5 stars
Spa pool
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 16 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 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 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 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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