A wooden gazebo by a pond with a large tree trunk nearby.

Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

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

Our top choices for Shelter Island hotels with a pool

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.
The entrance to The Harbor Front Inn with a double door and the address number 209.
Room

1. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NT$5,135
NT$6,797 total
includes taxes & fees
Nov 22 - Nov 23
The Harbor Front Inn
Property amenity
Front of property - evening/night
Bar (on property)
Terrace/patio

2. 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$11,060
NT$12,636 total
includes taxes & fees
Oct 31 - Nov 1
Shelter Island House
A poolside area with sun loungers, a pool, and a building with a balcony.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A cozy interior with a wooden bench, a sofa, and a bar area.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NT$7,335
NT$9,242 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 waterfront restaurant with outdoor seating and a view of the sea.
A coastal building with a deck extending over the water, featuring large windows and a dining area.
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$5,648
NT$7,384 total
includes taxes & fees
Nov 22 - Nov 23
Sound View Greenport
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 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.

5. 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$7,140
NT$8,157 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A poolside area with a hat and towel on a lounge chair.
A modern house with a deck, outdoor seating, and a fire pit.
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 rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

6. North Fork Resort

North Fork Resort
Greenport
NT$10,475
NT$11,967 total
includes taxes & fees
Oct 26 - Oct 27
North Fork Resort
Outdoor pool
A balcony with a view of the ocean, a lawn, and a house in the background.
Beach
A balcony with a view of the sea, a dining table, and a blue house in the background.

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
NT$5,510
NT$9,912 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
A pool area with umbrellas, potted plants, and a pathway leading to a building.
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.
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 splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
NT$11,443
NT$14,381 total
includes taxes & fees
Nov 22 - Nov 23
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.
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.
NT$4,336
NT$4,954 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt Place Long Island East End
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A bar area with shelves stocked with various bottles and glasses.
A large, white, two-story building with a covered porch and a bicycle parked in front.

10. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
NT$20,392
NT$23,412 total
includes taxes & fees
Oct 26 - Oct 27
Topping Rose House
View all properties

Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Top shelf - location, property, food and staff all great. Will be back."
Daniel 1-night trip
Posted 2 hours ago
Saybrook Point Resort & Marina
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"clean room"
Susan 1-night trip
Posted 1 day ago
Hyatt Place Long Island East End
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 2 days 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 3 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 3 days ago
Montauk Yacht Club
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."
Joan 2-night trip
Posted 3 days ago
Faraway Sag Harbor
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 are some accommodations with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool, and free self parking. Offshore Montauk: Features a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Offers a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Shelter Island?
Surround yourself with nature at Mashomack Preserve and Sunset Beach. Discover sights such as Shelter Island Historical Society, Wades Beach, and Crescent Beach during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be what you want if you come to town during the coldest months of January, February, or March when the average temperature is 38°F.

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