Hotels with Swimming Pool in Shelter Island Heights, New York

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Check prices for these dates

Tonight
Nov 15 - Nov 16
Tomorrow
Nov 16 - Nov 17
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Our top choices for Shelter Island Heights hotels with a pool

Pool

1. Seven - A Resort Style Inn

Seven - A Resort Style Inn
2.0 star property
Shelter Island Heights
The price is P24,260
P27,718 total
includes taxes & fees
Nov 20 - Nov 21
Seven - A Resort Style Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.

2. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (676 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is P8,613
P11,660 total
includes taxes & fees
Dec 13 - Dec 14
The Harbor Front Inn
A poolside area with sun loungers, a pool, and a building with a balcony.

3. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
  • cleanliness
    Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
The price is P11,471
P14,452 total
includes taxes & fees
Dec 2 - Dec 3
Oyster Estate
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, (768 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is P9,479
P12,650 total
includes taxes & fees
Dec 14 - Dec 15
Sound View Greenport
Terrace/patio

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is P12,241
P21,056 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
A poolside area with a hat and towel on a lounge chair.

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
The price is P20,475
P23,393 total
includes taxes & fees
Nov 16 - Nov 17
North Fork Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

7. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (689 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
The price is P13,956
P15,945 total
includes taxes & fees
Nov 16 - Nov 17
Sag Harbor Inn
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, (322 reviews)
  • cleanliness
    Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
The price is P19,787
P24,867 total
includes taxes & fees
Dec 6 - Dec 7
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.

9. Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
The price is P8,546
P9,763 total
includes taxes & fees
Nov 29 - Nov 30
Hyatt Place Long Island East End
A multi-story hotel with a swimming pool and outdoor seating area.

10. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Pristine waters await at this coastal retreat with private beach access and year-round pools.
The price is P8,877
P11,308 total
includes taxes & fees
Nov 22 - Nov 23
Water's Edge Resort & Spa
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 Heights

Breakfast included
4 stars

Frequently Asked Questions

How many pool hotels will I find in Shelter Island Heights?

Expedia has 10 hotels in Shelter Island Heights for your poolside break.

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.

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.