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 $115 ![](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 [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-24&endDate=2025-10-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shelter Island Heights Hotels with a Pool ![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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Blue Hotel Downtown Montauk 9.2/10 Wonderful (169) "The beach view is spectacular the surrounding area has everything you need for a each getaway" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $166 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9.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 Niantic 9.0/10 Wonderful (405) "Really enjoyed staying here. Relaxing and pet friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick CA $129 CA $149 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.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) ![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) ![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 (869) "Love this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $162 CA $192 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ### Montauk Manor Montauk 9.2/10 Wonderful (1257) "Beautiful grounds, excellent staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jess CA $212 CA $269 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/5c314659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Yacht Club Montauk 8.6/10 Excellent (1005) "Wonderful hotel and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FIONA CA $222 CA $414 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.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) ![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 Niantic 8.4/10 Very good (1010) "Small breakfast area lacked enough seating but otherwise a great stop near the casino. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theodore CA $109 CA $126 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.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/12000000/11960000/11951300/11951206/5e85d188.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) ![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 Clinton 8.6/10 Excellent (287) "Great staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler CA $109 CA $125 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.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) ![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) ### Hamlet Inn Southampton 8.6/10 Excellent (432) "A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $150 CA $194 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.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) ### Econo Lodge Inn & Suites Old Saybrook Westbrook Old Saybrook 7.2/10 Good (456) "the so-called breakfast was absolute minimum only thing available was make your own waffle" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $100 CA $115 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.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) ![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) ![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 (62) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $209 CA $399 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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=2025-11-07&endDate=2025-11-08®ionId=183716&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Shelter Island Heights Hotel Reviews ![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 "We love the stay everything was perfect" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great stay overall. Only suggestion would be to put a light on the side of the building. " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg) ### Marram 10/10 Excellent "We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful. " [](https://expedia.ca/Montauk-Hotels-Marram.h15408228.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 property, we loved our room, friendly staff. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![The Pridwin Hotel](//images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49_y.jpg) ### The Pridwin Hotel 10/10 Excellent "Nice property" [](https://expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.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 "The staff was amazing. Our room was insanely large and had a second room for the Whirlpool. It was listed as a second bedroom and was truly a second room complete with an air conditioner (or heater) and a tv. Our room didn’t have a bed in that room but I assume if you need it the have something available. Both rooms were clean and so were all the areas we were in. The breakfast was good and it was a pleasant place to meet up and visit with the other people in our party. " [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.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 "Our stay was just what we needed. Breakfast was full of choices and and plenty to eat and drink. A perfect stop in a lovely town." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Motel 6 Niantic, CT - New London](//images.trvl-media.com/lodging/2000000/1040000/1039700/1039681/0c062ad1_y.jpg) ### Motel 6 Niantic, CT - New London 10/10 Excellent "Convenient location and room was clean for a night crash. Needs some pest extermination as I noticed roaches escorting me out as I got ready to leave room for check out." [](https://expedia.ca/Niantic-Hotels-Motel-6-Niantic.h1039681.Hotel-Information) ![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg) ### Montauk Yacht Club 10/10 Excellent "Staffs were so kind. The place was peaceful and it is really a relaxing place to stay especially it is beach front" [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.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. Features a seasonal outdoor pool, an indoor pool, and a private beach. [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. Features sun loungers, an indoor pool, and complimentary wireless internet access. [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. [Montauk Blue Hotel](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information): Hotel, 6-minute walk from The Hamptons Beaches. Provides free self parking, a seasonal outdoor pool, and sun loungers. ### 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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