Title: Book the Best Shelter Island Ski Hotels in 2025 from CA $115 | Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Ski Hotels in Shelter Island, 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 Ski Hotels Tonight [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-19&endDate=2025-11-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shelter Island Ski Hotels No exact matches found, but these alternatives could be just right ## Recommended hotels in Shelter Island ![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/f2189685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/312e44f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/a1d1bd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Work and Play Special! Extended Stay Discount Shelter Island 10/10 Exceptional (52) "Really great property, had a relaxing lovely time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nava S. CA $1,007 CA $1,861 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor 8.0/10 Very good (1000) "Always a great stay at Pier Blue. Comfy bed and plenty of room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![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) ![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) ![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) ### Offshore Montauk Montauk 9.4/10 Exceptional (69) "Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $114 CA $210 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.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/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) ### Clinton Motel Clinton 8.6/10 Excellent (292) "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 Nov 30 - Dec 1 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e582d722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/58473cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/9177383b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort Greenport 9.4/10 Exceptional (6) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin CA $266 CA $304 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.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) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor Montauk 9.2/10 Wonderful (1262) "Always excellent, even suring my eleventh stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl CA $194 CA $249 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.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) ![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) ![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 Culloden Shores 8.4/10 Very good (876) "Very clean and spacious room! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Beth [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.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 Old Saybrook 7.2/10 Good (459) "🙂" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared CA $100 CA $115 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![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) ![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.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) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (535) "Awesome stay!!! Great Location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $152 CA $242 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/909788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stern at Soundview · Beach+Ocean+Sunrise Old Lyme 10/10 Exceptional (3) "I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lylian CA $106 CA $272 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.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. 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[All Inclusive Resorts and in Long Island](https://www.expedia.ca/Long-Island-Hotels-All-Inclusive-Hotel.0-0-d602887-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-Green-Sustainable.0-0-d602887-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Long Island](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Balconies.0-0-d602887-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Long Island](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d602887-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-LGBT-Friendly-Hotel.0-0-d602887-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Beach-Hotel.0-n129440-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Couples-Resorts-Hotels.0-n129440-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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[Mountain Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Mountain-Hotels.0-n129440-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Oceanfront-Hotels.0-n129440-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Winery-Hotel.0-n129440-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Midtown East](https://www.expedia.ca/Midtown-East-New-York-Hotels-Adults-Only-Resorts.0-n6141525-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [New York Hotels](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Luxury Hotels in Orient](https://www.expedia.ca/Orient-Hotels-Luxury-Hotel.0-0-d6326191-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Purchase](https://www.expedia.ca/Purchase-Hotels-Casino-Hotel.0-0-d6172129-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Purchase](https://www.expedia.ca/Purchase-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d6172129-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Spa Hotels in Purchase](https://www.expedia.ca/Purchase-Hotels-Spa-Hotel.0-0-d6172129-tSpaHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Queens](https://www.expedia.ca/Queens-New-York-Hotels-Adults-Only-Resorts.0-n149004-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Queens](https://www.expedia.ca/Queens-New-York-Hotels-Shopping-Hotel.0-n149004-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Hotels-Adults-Only-Resorts.0-0-d154327-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Hotels-Cheap-Hotels.0-0-d154327-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Hotels-Luxury-Hotel.0-0-d154327-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Hotels-Oceanfront-Hotels.0-0-d154327-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Hotels-Wedding-Hotels.0-0-d154327-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Beach-Hotel.0-0-d183716-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels) - 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