A pebbled beach with a sunset and a distant bridge.

Search Hotels with Swimming Pool in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Swimming Pool

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Shelter Island Heights hotels with a pool

Property amenity
Bar (on property)
Property amenity
Front of property – evening/night

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.
₹32,209
₹36,799 total
includes taxes & fees
31 Oct - 1 Nov
Shelter Island House
A swimming pool with a wooden deck, lounge chairs, and a fence.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A bar area with wooden bar stools and a bookshelf.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₹13,907
₹18,600 total
includes taxes & fees
22 Nov - 23 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.
A bedroom with a large bed, a window with curtains, a wall-mounted lamp, and a framed artwork.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
₹20,639
₹26,004 total
includes taxes & fees
25 Nov - 26 Nov
Oyster Estate
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A coastal building with a deck extending over the water, featuring large windows and a dining area.
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.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₹15,133
₹20,001 total
includes taxes & fees
22 Nov - 23 Nov
Sound View Greenport
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 living room with a sofa, a dining table, and a kitchen area in the background.

5. North Fork Resort

North Fork Resort
Greenport
₹29,488
₹33,690 total
includes taxes & fees
1 Nov - 2 Nov
North Fork Resort
Outdoor pool
A balcony with a view of the sea, a dining table, and a blue house in the background.
Terrace/patio
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.
₹16,047
₹28,867 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
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 spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

7. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
₹20,792
₹23,755 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 hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A spacious living room with a fireplace, comfortable seating, and large windows.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
₹33,325
₹41,881 total
includes taxes & fees
22 Nov - 23 Nov
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
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.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

9. 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.
₹12,627
₹14,427 total
includes taxes & fees
22 Nov - 23 Nov
Hyatt Place Long Island East End
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
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.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

10. 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.
₹17,859
₹22,175 total
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa
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 Vista Resort

Ocean Vista Resort

10/10 Excellent
"The location could not be more perfect! Right on the beach! The rooms are beautiful and spacious. We had to check in late and it could not be easier. We are really looking forward to our next stay here!"
Stefan 1-night trip
Posted 1 day ago
Ocean Vista Resort
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Always an amazing stay at Gurneys. The ocean views and the restorative spa alone make this place so special. The staff is friendly and the rooms are kept so clean. Highly recommended."
Peter 2-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
Svetlana 4-night trip
Posted 2 days ago
Montauk Yacht Club
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"Lovely view of the ocean. Bathroom was fine. Room was updated. Only had one nightstand and lamp."
harriet 2-night trip
Posted 4 days ago
Ocean Surf Resort
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 6 days ago
The Atlantic Hotel

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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