A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights Hotels with Swimming Pool

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Check availability on Shelter Island Heights Hotels with Swimming Pools

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

Our top choices for Shelter Island Heights hotels with a pool

Property amenity
Terrace/patio
Front of property – evening/night
Property amenity

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.
RM822
RM939 total
includes taxes & fees
7 Oct - 8 Oct
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 neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
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.
RM658
RM868 total
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A wooden cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
RM997
RM1,256 total
includes taxes & fees
2 Nov - 3 Nov
Oyster Estate
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
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.

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
RM784
RM1,012 total
includes taxes & fees
2 Nov - 3 Nov
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.
RM691
RM1,243 total
includes taxes & fees
1 Nov - 2 Nov
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 house with a deck, outdoor seating, and a fire pit.

6. North Fork Resort

North Fork Resort
Greenport
RM1,209
RM1,381 total
includes taxes & fees
7 Oct - 8 Oct
North Fork Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A hotel lobby with a sofa, chairs, tables, and a large window.

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.
RM895
RM1,022 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 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.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
RM1,674
RM2,103 total
includes taxes & fees
2 Nov - 3 Nov
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 formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

9. 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.
RM640
RM807 total
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
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 modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

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.
RM584
RM668 total
includes taxes & fees
3 Nov - 4 Nov
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
Hot tub
Spa

Top Shelter Island Heights Hotel Reviews

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"."
andrew 1-night trip
Posted 6 hours ago
Ocean Vista Resort
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Nice room close to beach"
Christina 2-night trip
Posted 8 hours ago
Ocean Resort Inn
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"My only complaint would be i wish there was a Keurig machine in the room instead of an espresso machine. Would definitely stay there again."
Fred 2-night trip
Posted 10 hours ago
The Atlantic Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Scenery was picture postcard perfect! Highly recommend balcony view from the main hotel Room service was excellent and the dining room staff and food were wonderful Only downside. There were no robes in the room and if you drank the bottled water, you were charged. Not really disclosed very well I'm actually planning on going back"
Billie 2-night trip
Posted 11 hours ago
Water's Edge Resort & Spa
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 1 day ago
Montauk Yacht Club
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 1 day ago
Ocean Surf Resort
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 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 21Β°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 3Β°C.

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