Find Hotels with a Pool in Shelter Island Heights, NY from CA $115

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Shelter Island Heights Hotels with a Pool

Our top choices for Shelter Island Heights hotels with a pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (106 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is CA $159
CA $260 total
includes taxes & fees
Mar 5 - Mar 6
Offshore Montauk

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is CA $107
CA $123 total
includes taxes & fees
Feb 24 - Feb 25
Clinton Motel

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is CA $180
CA $243 total
includes taxes & fees
Feb 22 - Feb 23
Windward Shores Ocean Resort

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
2.5 star property
Niantic
9.0 out of 10, Wonderful, (479 reviews)
"Nice place to stay"
United States
Tomasz
The price is CA $119
CA $137 total
includes taxes & fees
Feb 22 - Feb 23
Best Western Niantic - New London/Mystic Area

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,008 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is CA $133
CA $153 total
includes taxes & fees
Feb 26 - Feb 27
Quality Inn Old Saybrook - Westbrook

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (888 reviews)
"Big room Clean Needs bathroom update In general, we had a good day"
United States
Raz
Kenny's Tipperary Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (453 reviews)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is CA $118
CA $153 total
includes taxes & fees
Feb 21 - Feb 22
Hamlet Inn

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (207 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is CA $144
CA $171 total
includes taxes & fees
Feb 21 - Feb 22
Southampton Long Island Hotel

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
2.5 star property
Niantic
8.4 out of 10, Very good, (1,005 reviews)
"nice, clean hotel. "
United States
Amber
The price is CA $100
CA $115 total
includes taxes & fees
Mar 12 - Mar 13
Sleep Inn & Suites Niantic North

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,297 reviews)
"Nice pool, great restaurant "
United States
April
The price is CA $158
CA $207 total
includes taxes & fees
Mar 2 - Mar 3
Montauk Manor
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.

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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Top Shelter Island Heights Hotel Reviews

Frequently asked questions

What are the best hotels in Shelter Island Heights with outdoor pools?
The Pridwin Hotel is a fantastic 4-star option in Shelter Island Heights, boasting an impressive review rating of 9.6 from travellers who rave about its beautiful and clean rooms. This hotel features a stunning outdoor pool surrounded by sun loungers, making it an ideal spot for families looking to relax and soak up the sun.

Guests particularly enjoy the poolside bar, where refreshing drinks can be enjoyed while taking in the breathtaking partial ocean and water views. Additionally, The Pridwin offers complimentary continental breakfast, ensuring that families can start their day off right before heading out to explore the beautiful surroundings.
How much does a hotel with outdoor pool in Shelter Island Heights cost?
Enjoy staying in a hotel in Shelter Island Heights with an outdoor pool. You can find a great deal from CA $115 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What are some of the best Shelter Island Heights hotels with outdoor pools and scenic views?
The Pridwin Hotel is a stunning 4-star destination that combines comfort with breathtaking views, earning an impressive traveller rating of 9.6. Nestled amidst the serene beauty of Shelter Island Heights, this hotel features an inviting outdoor pool where guests can relax on sun loungers while enjoying sweeping views of the ocean and water.

What truly sets The Pridwin apart is its picturesque setting, offering both partial ocean and sea views, making every moment spent by the pool a feast for the eyes. Guests rave about the delicious food options available, ensuring that your family can enjoy a delightful dining experience after a day of adventure.

In addition to its stellar pool area, The Pridwin provides complimentary continental breakfast, making mornings a breeze for families looking to fuel up for a day of exploration.
Are there hotels in Shelter Island Heights with outdoor pool cabanas or loungers?
The Pridwin Hotel is a charming 4-star destination in Shelter Island Heights that offers a delightful outdoor pool experience, superb for families seeking relaxation and fun. With a stellar traveller rating of 9.6, guests rave about the beautiful and clean rooms, as well as the amazing amenities.

At The Pridwin, you'll find inviting poolside loungers where you can soak up the sun or unwind after a day of exploring. The hotel features a poolside bar, making it convenient to enjoy refreshing beverages without leaving your lounge chair. Additionally, the property boasts stunning views of the ocean and partial sea views, enhancing your overall experience.

Families will appreciate the complimentary continental breakfast, setting the stage for a great start to your day.
Which Shelter Island Heights hotels offer poolside service for food and drinks?
The Pridwin Hotel is a delightful 4-star option in Shelter Island Heights that stands out for its inviting poolside service, allowing guests to enjoy food and drinks right by the water. With a remarkable traveller rating of 9.6, this hotel is praised for its beautiful and clean rooms, as well as its amazing amenities and delicious food.

Nestled amidst stunning views, The Pridwin features a pool area complete with sun loungers, and a poolside bar where you can unwind with a refreshing drink or a tasty bite. Whether you're soaking up the sun or enjoying a leisurely afternoon swim, the combination of excellent service and scenic surroundings makes for a superb getaway.
Is it cheaper to book flights and a hotel in Shelter Island Heights as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
How can I save on a hotel in Shelter Island Heights with Expedia?
Before booking your Shelter Island Heights hotel, remember to join Expedia's free travel rewards program—One Key™. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Shelter Island Heights for you.

Explore a world of travel with Expedia