Find Hotels with a Pool in Shelter Island, NY

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Check prices for these dates

Tonight
7 Nov - 8 Nov
Tomorrow
8 Nov - 9 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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.

1. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (674 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is AED 514
AED 692 total
includes taxes & fees
15 Nov - 16 Nov
The Harbor Front Inn
A poolside area with sun loungers, a pool, and a building with a balcony.

2. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (301 reviews)
  • cleanliness
    Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
The price is AED 691
AED 870 total
includes taxes & fees
15 Nov - 16 Nov
Oyster Estate
Pool

3. Seven - A Resort Style Inn

Seven - A Resort Style Inn
2.0 star property
Shelter Island Heights
The price is AED 1,523
AED 1,740 total
includes taxes & fees
25 Nov - 26 Nov
Seven - A Resort Style Inn
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.

4. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (766 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is AED 560
AED 745 total
includes taxes & fees
23 Nov - 24 Nov
Sound View Greenport
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

5. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (686 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
The price is AED 804
AED 919 total
includes taxes & fees
8 Nov - 9 Nov
Sag Harbor Inn
Outdoor pool

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is AED 632
AED 1,129 total
includes taxes & fees
30 Nov - 1 Dec
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

7. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
The price is AED 1,180
AED 1,348 total
includes taxes & fees
8 Nov - 9 Nov
North Fork Resort
A pool area with umbrellas, potted plants, and a pathway leading to a building.

8. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (320 reviews)
  • cleanliness
    Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
The price is AED 1,190
AED 1,496 total
includes taxes & fees
6 Dec - 7 Dec
Faraway Sag Harbor
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

9. A Room At The Beach

A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (105 reviews)
  • cleanliness
    Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
The price is AED 1,088
AED 1,243 total
includes taxes & fees
8 Nov - 9 Nov
A Room At The Beach
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

10. Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (210 reviews)
  • cleanliness
    Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
The price is AED 810
AED 1,018 total
includes taxes & fees
22 Nov - 23 Nov
Journey East Hampton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
Greenport

10/10 Excellent

everything was excellent. The only comment I would have is that the hallways smelled funny. Maybe if they could put a more fresh aroma and that’ll be great. Staff, everything was awesome.
United States
Maureen
Reviewed October 22, 2023
The Harbor Front Inn

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.