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
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Shelter Island Heights hotels with a pool

Property amenity
Property amenity
Terrace/patio
Bar (on property)

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$6,412
NT$7,325 total
includes taxes & fees
Oct 6 - Oct 7
Shelter Island House
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
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.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NT$5,133
NT$6,774 total
includes taxes & fees
Nov 1 - Nov 2
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.
A wooden cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NT$8,284
NT$10,437 total
includes taxes & fees
Nov 1 - Nov 2
Oyster Estate
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 coastal building with large windows, a deck, and a view of the sea at sunset.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
NT$6,109
NT$7,889 total
includes taxes & fees
Nov 2 - Nov 3
Sound View Greenport
Outdoor pool
Beach
Room
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.
NT$5,385
NT$9,688 total
includes taxes & fees
Nov 1 - Nov 2
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 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.

6. North Fork Resort

North Fork Resort
Greenport
NT$8,488
NT$9,697 total
includes taxes & fees
Oct 7 - Oct 8
North Fork Resort
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 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.

7. 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$6,978
NT$7,972 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
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.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

8. 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$4,970
NT$5,679 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Long Island East End
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 spacious living room with a fireplace, comfortable seating, and large windows.
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$13,047
NT$16,397 total
includes taxes & fees
Nov 2 - Nov 3
Faraway Sag Harbor
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.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

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.
NT$4,994
NT$6,293 total
includes taxes & fees
Nov 1 - Nov 2
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Montauk Yacht Club was the perfect getaway for my boyfriend and I to celebrate our 3 year anniversary. Our room was spotless and had a great view of the water. We did mention to them ahead of time that it was our anniversary, thinking they might have some champagne or something waiting in the room for us, but they did not. Nonetheless, it was still a perfect stay. We played tennis and the courts were beautiful. The on-site restaurant was very yummy as well! I definitely recommend coming during the off season, as it is way less crowded in town and very relaxing."
Sarah 3-night trip
Posted 13 hours ago
Montauk Yacht Club
Sun N Sound

Sun N Sound

8/10 Good
"Everything was fine accept there really wasn’t any privacy people and staff were always by room and outdoor space"
Joseph 2-night trip
Posted 13 hours ago
Sun N Sound
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 17 hours ago
Ocean Surf Resort
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The property was definitely worth a five-star rating and the views of the Bay were tremendous! The rooms were very clean and the beds were super comfortable. I had a wonderful breakfast looking out over the water. It was magical"
Melanie 1-night trip
Posted 3 days ago
Water's Edge Resort & Spa
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Such a great spot! Clean, easy access, everything you need!!"
Christian 3-night trip
Posted 4 days ago
Ocean Resort Inn
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beachcomber was wonderful loved it"
elizabeth 3-night trip
Posted 5 days ago
Beachcomber Resort at Montauk

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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