Title: Book the Best Hotels with POOL in Shelter Island Heights in 2026 | Expedia.ca [Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)[Shelter Island Heights Vacation Packages](https://expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) ![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brian V. Rowe # Find Hotels with a Pool in Shelter Island Heights, NY from CA $106 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Shelter Island Heights Hotels with a Pool Tonight [Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-03&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 4 - Jan 5](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-04&endDate=2026-01-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island Heights hotels with a pool ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w1536h1018x0y0-00be5d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/20551fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/708b4a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily self-serve breakfast for a fee](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/c2934dcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Niantic - New London/Mystic Area [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) Niantic 9.0/10 Wonderful (454) "Clean rooms, included breakfast, decent gym all at a reasonable price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $124 CA $143 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6f247566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) Montauk 9.4/10 Exceptional (92) "Hotel was beautiful !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $159 CA $260 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/efe89d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/8fa06225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) Culloden Shores 8.4/10 Very good (880) "Really clean and nice location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiara [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) Montauk 9.2/10 Wonderful (1276) "The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $190 CA $244 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/1345db22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (557) "Room and staff were amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $185 CA $251 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, beach towels](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8a104c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) Southampton 8.6/10 Excellent (445) "Great weekend stay! staff was super kind and property was beautiful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chyanne CA $120 CA $155 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d45c604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clinton Motel [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) Clinton 8.6/10 Excellent (298) "Great staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler CA $107 CA $123 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/cee0fa4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/98c458f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach [](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) Water Mill 10/10 Exceptional (6) "Highly recommend everything from start to finish went smoothly and it was a great experience!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie M. CA $5,750 CA $10,019 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/f4e648ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Old Saybrook Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) Old Saybrook 7.2/10 Good (464) "We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $92 CA $106 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.6/10 Excellent (602) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $206 CA $275 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2026-01-17&endDate=2026-01-18®ionId=183716&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Shelter Island Heights Hotel Reviews ![Sleep Inn & Suites Niantic North](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg) ### Sleep Inn & Suites Niantic North 10/10 Excellent "It’s a cute hotel, nice and clean. Beds are very clean and very comfortable and nice breakfast too." [](https://expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Nice place" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great place!" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Spacious, clean room with water view! Anthony, the bellboy was awesome. He lifted our bags and shuttled us to and fro to The Kate in good time for our concert eve! The spa treatment was perfect. We loved taking a dip in the heated outdoor pool the next day!" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Best Western Niantic - New London/Mystic Area](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9_y.jpg) ### Best Western Niantic - New London/Mystic Area 10/10 Excellent "The best western niantic is clean, comfortable, and very reaonably priced. The staff is very friendly and the complimentary breakfast is well kept up. This hotel is a great bargain" [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "Good room. Great view! Nice heating system. Friendly staff. " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Motel 6 Niantic, CT - New London](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039681/0c062ad1_y.jpg) ### Motel 6 Niantic, CT - New London 10/10 Excellent "Great !!" [](https://expedia.ca/Niantic-Hotels-Motel-6-Niantic.h1039681.Hotel-Information) ![Sea Crest Resort](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Lovely, clean 1 bedroom with spectacular view" [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable" [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Shelter Island Heights with outdoor pools? > 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? ### What are some of the best Shelter Island Heights hotels with outdoor pools and scenic views? > 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? > 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? > 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? ### How can I save on a hotel in Shelter Island Heights with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Beach-Hotel.0-0-d177851-tBeachHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Business-Hotel.0-0-d177851-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Honeymoon-Hotels.0-0-d177851-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Hotels-With-Waterslides.0-0-d177851-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - 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