Shelter Island Heights Hotel Guide - Hotels with Pool in Shelter Island Heights, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island Heights Hotels with Pool

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

Our top choices for Shelter Island Heights hotels with a pool

Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
"The staff at the front desk and the pool bar were extremely friendly and laid back."
United States
Elizabeth
The price is €364
includes taxes & fees
28 May - 29 May
The Pridwin Hotel
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very good, (37 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
"Used the pool at reciprocal property."
United States
Annmarie
The price is €215
includes taxes & fees
31 May - 1 Jun
West Neck Guesthouse
Property amenity

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (57 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
"Enjoyed the pool once the weather cooperated, nice and secluded."
United States
Christine
The price is €198
includes taxes & fees
4 Jun - 5 Jun
Shelter Island House
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (189 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
"The pool is nice and it was great having a restaurant on site!"
United States
Elizabeth
The price is €123
includes taxes & fees
25 May - 26 May
Breakers Montauk
Seasonal outdoor pool, pool loungers

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
"It was a very cozy room and love the fact that it was right next to the beach"
United States
Rodney
The price is €143
includes taxes & fees
25 May - 26 May
Ocean Resort Inn
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (311 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
"The pool was great"
United States
Michelle
The price is €78
includes taxes & fees
1 Jun - 2 Jun
Clinton Motel
Seasonal outdoor pool, pool loungers

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (498 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
"Pool is nice!"
United States
Cassidy
The price is €123
includes taxes & fees
25 May - 26 May
Aqualina Inn Montauk
Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (893 reviews)
  • cleanliness
    Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.
"loved the pet friendly aspect "
United States
jane
The price is €129
includes taxes & fees
26 May - 27 May
Kenny's Tipperary Inn
Two-Bedroom Suite

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
"The hotel was very clean and the location was very good. It was close to restaurants and beach."
United States
Anonymous traveller
The price is €236
includes taxes & fees
26 May - 27 May
The Penny Lane
Outdoor pool, pool umbrellas, pool loungers

Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
"It is right by the beach and close to restaurants and a market."
United States
Beatriz
The price is €301
includes taxes & fees
9 Jun - 10 Jun
Offshore Montauk
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.
View all properties

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

Breakfast included
4 stars

Top Shelter Island Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

6/10 Okay
"Nice location, well maintained grounds, the buildings are old, old bathrooms, not well controlled temperature in the guest rooms, some of the staff is not very welcoming."
Slava 1-night trip
Posted 4 hours ago
Water's Edge Resort & Spa

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 Pridwin Hotel: Features a private beach, a seasonal outdoor pool and a full-service spa. Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Pier Blue Inn Old Saybrook - Essex: Hotel, 5-minute walk from The Hamptons Beaches. Offers 2 outdoor swimming pools, a children's pool and a private beach. Montauk Yacht Club: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
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.