A pebbled beach with a sunset and a distant bridge.

Hotels with Swimming Pools in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Swimming Pools

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 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.
S$294
includes taxes & fees
13 Oct - 14 Oct
Shelter Island House
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
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.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
S$277
includes taxes & fees
4 Nov - 5 Nov
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 scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A beach bar with wooden chairs and a small table, overlooking the sea.

3. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
S$283
includes taxes & fees
3 Nov - 4 Nov
Sound View Greenport
Outdoor pool
Room
Beach
Room

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
S$389
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
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 desk with drawers, a chair, a lamp, and a framed picture on the wall.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.

5. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
S$418
includes taxes & fees
8 Nov - 9 Nov
Oyster Estate
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 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
S$346
includes taxes & fees
19 Oct - 20 Oct
North Fork Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
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.
A waterfront property with a large house, multiple boats docked, and lush greenery.

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.
S$320
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
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.

8. 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.
S$209
includes taxes & fees
26 Oct - 27 Oct
The Bentley Hotel Southampton
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
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.
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

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.
S$299
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa
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 dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A spacious living room with a fireplace, comfortable seating, and large windows.

10. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
S$608
includes taxes & fees
8 Nov - 9 Nov
Faraway Sag Harbor
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"We had a fantastic stay here. It was beautiful, clean and the staff was excellent. We will be back."
Jennifer L 1-night trip
Posted 10 hours ago
Water's Edge Resort & Spa
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great"
Linda 2-night trip
Posted 3 days ago
Gurney's Montauk Resort & Seawater Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"."
andrew 1-night trip
Posted 4 days ago
Ocean Vista Resort
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 4 days ago
Montauk Yacht Club
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 5 days 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 9 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 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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