Title: Visit Shelter Island Heights: Best of Shelter Island Heights Tourism | Expedia Travel Guide - 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) # Shelter Island Heights ## Travel Guide ![Photo by Erisa Dilo](https://mediaim.expedia.com/destination/2/4941e2fd68ce17b39e6de73e44df4c4b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Erisa Dilo](https://mediaim.expedia.com/destination/2/4941e2fd68ce17b39e6de73e44df4c4b.jpg) ![Photo by tom owens](https://mediaim.expedia.com/destination/2/0e1f0e7d1a701f494768ac33b98360ed.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by tom owens](https://mediaim.expedia.com/destination/2/0e1f0e7d1a701f494768ac33b98360ed.jpg) ![Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg) ![Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/0a5ae411b4c93890031f6a363b4609fd.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/0a5ae411b4c93890031f6a363b4609fd.jpg) ## Visit Shelter Island Heights Where to stay Things to do ### Where to stay in Shelter Island Heights ![Default Image](https://mediaim.expedia.com/destination/2/4941e2fd68ce17b39e6de73e44df4c4b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Heights If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing. [](https://expedia.ca/Shelter-Island-Heights-The-Heights.dx553248635976473534) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Hay Beach Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out. [](https://expedia.ca/Shelter-Island-Hay-Beach.dx553248635976470037) - Shelter Island Heights Hotel Deals - Vacation Rentals in Shelter Island Heights ![The Pridwin Hotel](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Pridwin Hotel 81 Shore Road, Shelter Island Heights, NY CA $479 CA $602 total Oct 19 - Oct 20 includes taxes & fees Stay at this 4-star beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ... 9.4/10 Exceptional! (82 reviews) "Nice property" Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=6473437&PinnedHotelID=6473437&HadPinnedHotel=true®ionId=183716) ![The Chequit](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/3084ead9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Chequit 23 Grand Ave, Shelter Island Heights, NY CA $380 CA $435 total Nov 2 - Nov 3 includes taxes & fees Stay at this 3-star hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and ... 8.8/10 Excellent! (37 reviews) "A cozy room with great pillows and quiet. Perfect little place." Reviewed on Oct 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=67569836&PinnedHotelID=67569836&HadPinnedHotel=true®ionId=183716) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd, Old Saybrook, CT CA $112 CA $129 total Oct 19 - Oct 20 includes taxes & fees Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ... 7.8/10 Good! (1,013 reviews) "We had a quick stop in the area and picked this hotel. We weee pleasantly surprised! It’s rare to find a small private hotel maintained like a corporate hotel. This is a good one." Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=183716) [See all 4,752 properties in Shelter Island Heights](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=183716) 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. ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Manor 236 Edgemere St., Montauk, NY Stay at this 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ... 9/10 Wonderful! (1,253 reviews) "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." Reviewed on Oct 6, 2025 [](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Windward Shores Ocean Resort](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/23c43d21_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Windward Shores Ocean Resort 2062 Montauk Highway, PO Box 7031, Amagansett, NY Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ... 8.6/10 Excellent! (296 reviews) "The non ocean view rooms are fabulous. I’m sure the ocean side ones are great." Reviewed on Sep 30, 2025 [](https://expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) ![Montauk Oceanside Suites](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/4604b12d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Oceanside Suites 115 South Emerson Avenue, Montauk, NY Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ... 8.4/10 Very Good! (414 reviews) "Property was clean and nice but did not smell good inside, it need candles and air freshener, also think something was off about the sewage system" Reviewed on Sep 16, 2025 [](https://expedia.ca/Montauk-Hotels-Born-Free-Suites-By-The-Sea.h11062836.Hotel-Information) [See all properties in Shelter Island Heights](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=183716&sort=VACATION_RENTAL) 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. ## Check Shelter Island Heights hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-15&endDate=2025-10-16) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-15&endDate=2025-10-16) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-15&endDate=2025-10-16) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-15&endDate=2025-10-16)[Oct 15 - Oct 16](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-15&endDate=2025-10-16) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-16&endDate=2025-10-17) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-16&endDate=2025-10-17) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-16&endDate=2025-10-17) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-16&endDate=2025-10-17)[Oct 16 - Oct 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=2025-10-16&endDate=2025-10-17) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025)[Oct 17 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)[Oct 24 - Oct 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183716&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) ### Popular places to visit #### Sunset Beach Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene. [](https://expedia.ca/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction) #### Crescent Beach Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene. [](https://expedia.ca/Crescent-Beach-Shelter-Island-Heights.d553248621554204758.Vacation-Attraction) #### Shelter Island Country Club Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets. [](https://expedia.ca/Shelter-Island-Country-Club-New-York.d6282167.Vacation-Attraction) ### Things to do ![Join a small group full-day wine tour with a certified Sommelier host](https://mediaim.expedia.com/localexpert/1350908/45c47e3f-3e0f-448e-a1a4-64596ec183f0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Long Island Wine and Food Day Trip with Sommelier host from NYC CA $206 per adult [](https://expedia.ca/things-to-do/long-island-wine-and-food-day-trip-with-sommelier-host-from-nyc.a1350908.activity-details) ![Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting](https://mediaim.expedia.com/localexpert/48343602/e3615e6b-a5d4-472f-b85c-80434f787622.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Mattituck: North Fork Area Bike Tour with Food Tasting CA $195 per adult [](https://expedia.ca/things-to-do/from-mattituck-north-fork-area-bike-tour-with-food-tasting.a48343602.activity-details) [See all activities in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities) ## Cities near Shelter Island Heights ![Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Shelter Island [](https://expedia.ca/Shelter-Island.dx157359) ![Photo by Benny Goh ](https://mediaim.expedia.com/destination/2/64a7a541b17dabdb743e9908dec5b467.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Marion [](https://expedia.ca/East-Marion.dx6069914) ![Orient](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Orient [](https://expedia.ca/Orient.dx6326191) ![Photo by Nina Dinoff](https://mediaim.expedia.com/destination/2/9a9f855657c0f02d64549df7b59e54eb.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Greenport West [](https://expedia.ca/Greenport-West.dx553248635975876381) - Cities near Shelter Island Heights - Places of interest [Shelter Island](https://expedia.ca/Shelter-Island.dx157359)[East Marion](https://expedia.ca/East-Marion.dx6069914)[Orient](https://expedia.ca/Orient.dx6326191)[Dering Harbor](https://expedia.ca/Dering-Harbor.dx553248634998885605)[Greenport West](https://expedia.ca/Greenport-West.dx553248635975876381) - [Ocean Beach Park](https://expedia.ca/Ocean-Beach-Park-New-London.d6071449.Vacation-Attraction) - [Cooper's Beach](https://expedia.ca/Coopers-Beach-Southampton.d6326842.Vacation-Attraction) - [East Hampton Main Beach](https://expedia.ca/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction) - [Essex Steam Train](https://expedia.ca/Essex-Steam-Train-Essex.d6171206.Vacation-Attraction) - [Wolffer Estates Vineyard](https://expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction) - [Hither Hills State Park](https://expedia.ca/Hither-Hills-State-Park-Montauk.d553248621532665771.Vacation-Attraction) - [Ditch Plains Beach](https://expedia.ca/Ditch-Plains-Beach-Montauk.d6326860.Vacation-Attraction) - [Kontokosta Winery](https://expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Pindar Vineyards](https://expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction) - [Lake Montauk](https://expedia.ca/Lake-Montauk-Montauk.d553248621532665766.Vacation-Attraction) - [Shinnecock Nation Cultural Center and Museum](https://expedia.ca/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)