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 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Shelter Island Heights hotels with a pool

Property amenity
Front of property - evening/night
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$6,521
NT$7,450 total
includes taxes & fees
Oct 21 - Oct 22
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 hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
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.
NT$5,800
NT$7,552 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
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 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.
NT$7,290
NT$9,185 total
includes taxes & fees
Oct 26 - Oct 27
Oyster Estate
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
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.
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.
NT$5,822
NT$7,580 total
includes taxes & fees
Nov 16 - Nov 17
Sound View Greenport
Outdoor pool
Beach
Room
Terrace/patio

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$5,495
NT$9,884 total
includes taxes & fees
Nov 12 - Nov 13
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 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 house with a deck, outdoor seating, and a fire pit.

6. North Fork Resort

North Fork Resort
Greenport
NT$10,445
NT$11,933 total
includes taxes & fees
Oct 21 - Oct 22
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$7,096
NT$8,107 total
includes taxes & fees
Nov 2 - Nov 3
Sag Harbor Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
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 splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
NT$11,995
NT$15,075 total
includes taxes & fees
Nov 16 - Nov 17
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.
A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.
A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

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.
NT$4,129
NT$4,717 total
includes taxes & fees
Nov 3 - Nov 4
Hyatt Place Long Island East End
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A living room with two sofas, a coffee table, a lamp, and a painting on the wall.
A dining area with tables and chairs, a clock on the wall, and a counter with food items.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.

10. 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.
NT$3,140
NT$3,611 total
includes taxes & fees
Nov 9 - Nov 10
Quality Inn Old Saybrook - Westbrook
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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Room was spacious, comfortable and clean. Overall the hotel was nice. The decorating was a bit off putting and looked like it had been done in the 1970’s and never changed; orange and avocado green with brown carpet. If you can get past that it was a good place to stay. Breakfast was very nice with plenty of hot and cold choices. For me, the fact that it was open from 7:30 til 10 am was very nice. I would stay here again."
Brenda 4-night trip
Posted 16 hours ago
Quality Inn Old Saybrook - Westbrook
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 19 hours ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

8/10 Good
"This was our third stay at Soundview. We stay there because all of the rooms face the sound and the natural view can’t be beat. The rooms are lodgy but spacious and depending on your room, there are public/private balconies."
Danielle 1-night trip
Posted 2 days ago
Sound View Greenport
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Great place in Montauk. Beautiful view and room was spacious."
fred 4-night trip
Posted 4 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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