Title: Book the Best Hotels with POOL in Shelter Island Heights in 2025 | 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) ![](https://mediaim.expedia.com/destination/2/4941e2fd68ce17b39e6de73e44df4c4b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Erisa Dilo # Find Hotels with a Pool in Shelter Island Heights, NY from CA $125 - ![](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 [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-01&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-02&endDate=2025-11-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/20551fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Niantic - New London/Mystic Area Niantic 9.0/10 Wonderful (416) "The rooms were very clean. Staff was friendly and helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $129 CA $149 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Indoor pool, open 10:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/bd8b651c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium King Ocean Front](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/720dfd39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Ocean Front | Balcony view](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/d8d28e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Blue Hotel Downtown Montauk 9.2/10 Wonderful (174) "It is aperfect no-frills hotel right on the beach at an extremely reasonable price, walkable to great dining, shopping and more" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tod CA $162 CA $186 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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) ![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) ![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) ### Kenny's Tipperary Inn Culloden Shores 8.4/10 Very good (870) "Love this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan [](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) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.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) ### Montauk Manor Montauk 9.2/10 Wonderful (1260) "Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lydia CA $194 CA $249 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.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) ![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk Montauk 9.4/10 Exceptional (64) "Great place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julien CA $156 CA $339 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (526) "Beautiful view and room. Staff friendly and accommodating. Excellent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $192 CA $288 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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 Greenport 8.6/10 Excellent (584) "Beautiful Long Island Sound and sunset views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stuart CA $192 CA $288 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/f1ad96fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/7abafcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New and Modern Bridgehampton Accommodations Bridgehampton 9.6/10 Exceptional (15) "Had a great stay here with a small group. Host was very accommodating and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa M. CA $246 CA $604 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.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/aafb0c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/81065c8c.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) ### Sleep Inn & Suites Niantic North Niantic 8.4/10 Very good (1013) "Nice place, have stayed here a few times, decent breakfast , clean and the bed was really comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $109 CA $125 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/e408e278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/0c1795de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Pool View](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/d576d9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lower 2 Bedroom 2 Bath Corner Oceanfront | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5d8554d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Crest Resort Amagansett 9.2/10 Wonderful (500) "Perfect location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bernadette CA $254 CA $320 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.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=2025-11-15&endDate=2025-11-16®ionId=183716&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Shelter Island Heights Hotel Reviews ![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg) ### Marram 10/10 Excellent "Wonderful stay! Spacious and elegant room, friendly staff, breathtaking view. Memorable birthday weekend. " [](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Perfect " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Beautiful Long Island Sound and sunset views." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Best Western Niantic - New London/Mystic Area](//images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9_y.jpg) ### Best Western Niantic - New London/Mystic Area 10/10 Excellent "Clean room friendly staff" [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Sleep Inn & Suites Niantic](//images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg) ### Sleep Inn & Suites Niantic 10/10 Excellent "Room was clean and comfy. " [](https://expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Everything was good, had a quiet happy stay." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](//images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely" [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "The staff is extremely helpful and polite. The location is wonderful with a beautiful ocean view. I can’t say enough nice things about it!" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Beautiful hotel in the marine. CT summer playground. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ## Frequently asked questions ### 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 Pridwin Hotel](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information): Features a private beach, a seasonal outdoor pool, and a full-service spa. [The Chequit](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information): Resort, 13-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool, and a private beach. [Gurney's Montauk Resort & Seawater Spa](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information): Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Pier Blue Inn Old Saybrook - Essex](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information): Hotel, 1-minute walk from The Hamptons Beaches. Offers sun loungers, an indoor pool, and complimentary wireless internet access. [Best Western Niantic - New London/Mystic Area](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information): Provides buffet, an indoor pool, and free self parking. ### 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 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. ## 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) - [Ski Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Ski-Hotel.0-0-d177851-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Waterpark-Hotels.0-0-d177851-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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