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 [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-20&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-21&endDate=2025-12-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island Heights hotels with a pool ![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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.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) ![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) ### Offshore Montauk [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) Montauk 9.2/10 Wonderful (82) "Nice decoration, clean amenities, good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) weihao CA $160 CA $261 total includes taxes & fees Jan 11 - Jan 12, 2026 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.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) ### Kenny's Tipperary Inn [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) Culloden Shores 8.4/10 Very good (879) "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) ![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.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) ![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 (1270) "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 $191 CA $245 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9.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 (450) "Easy check in and check out, comfortable bed, clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $127 CA $146 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.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 (548) "Awesome stay!!! Great Location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $185 CA $279 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.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 (461) "A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $92 CA $106 total includes taxes & fees Jan 4 - Jan 5, 2026 [](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) ![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) ![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) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.6/10 Excellent (598) "Staff was amazing , room clean view phenomenal " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $219 CA $318 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/a58a238d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/aafb0c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/c8355f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Niantic North [](https://www.expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) Niantic 8.4/10 Very good (1000) "Clean Room/Polite staff/ Breakfast was basic/ pool area looked maintained." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara CA $112 CA $129 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (400) "great cost-effective option; room was very spacious and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isadora CA $173 CA $199 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/abb4b75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/2fdf39bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/77f9f5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hero King Patio Deluxe | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/65048075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hero Beach Club [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) Montauk 9.0/10 Wonderful (202) "Great weekend trip " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $197 CA $365 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.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=2026-01-03&endDate=2026-01-04®ionId=183716&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Shelter Island Heights Hotel Reviews ![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 "Everything was perfect. Staff, room, experience. Will definitely stay again. " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "The staff was friendly. The room was good. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 "Friendly and helpful staff, wonderful dining experience at Fresh Salt" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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 "Holiday family tradition!" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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 "Clean, quiet, and staff was super professional. " [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![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 "Very clean room Did not have the breakfast as we left prior to it starting. Would stay there again " [](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 "Great room with amazing views! Staff was fantastic and the food was great too" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Beachcomber Resort at Montauk](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 10/10 Excellent "Beautiful views and so close to town. Walk right down the driveway to the ocean! " [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![Shelter Island House](https://images.trvl-media.com/lodging/15000000/15000000/14997600/14997595/efd291ed_y.jpg) ### Shelter Island House 8/10 Good "One staff member was there to check us in. He was helpful in bringing our bags to our room. He also suggested several restaurants for us to try." [](https://expedia.ca/Shelter-Island-Heights-Hotels-Shelter-Island-House.h14997595.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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