Title: Book the Best Gloucester Ski Hotels in 2026 from CA $157 | Expedia.ca [Gloucester Travel Guide](https://expedia.ca/Gloucester.dx8008)[Hotels in Gloucester](https://expedia.ca/Gloucester-Hotels.d8008.Travel-Guide-Hotels)[Vacation Rentals in Gloucester](https://expedia.ca/Gloucester-Vacation-Rentals.d8008.Travel-Guide-VacationRentals)[Flights to Gloucester](https://expedia.ca/Cheap-Flights-To-Gloucester.d8008.Travel-Guide-Flights)[Things to do in Gloucester](https://expedia.ca/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities)[Gloucester Car Rentals](https://expedia.ca/Car-Rentals-In-Gloucester.d8008.Car-Rental-Guide)[Gloucester Vacation Packages](https://expedia.ca/Gloucester.d8008.Destination-Travel-Guides) ![Good Harbor Beach featuring a sunset, a sandy beach and general coastal views](https://images.trvl-media.com/place/553248621532667409/fda0f2a2-9a66-4e87-a0d4-6552f49b1eaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248621532667409/fda0f2a2-9a66-4e87-a0d4-6552f49b1eaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Gloucester Ski Hotels Tonight [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8008&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=8008&startDate=2026-01-18&endDate=2026-01-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8008&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8008&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Gloucester ski hotels ![Beach](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/e13dffe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/a5aee65c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/aa6d7b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/6c9fe3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wylie Inn and Conference Center at Endicott College [](https://www.expedia.ca/Boston-Hotels-The-Wylie-Inn-And-Conference-Center-At-Endicott-College.h1886884.Hotel-Information) Beverly 9.2/10 Wonderful (1,160 reviews) "Easy and ample parking, friendly and helpful staff, will stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $140 CA $157 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-The-Wylie-Inn-And-Conference-Center-At-Endicott-College.h1886884.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/30000000/29860000/29855500/29855495/b8e12171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/30000000/29860000/29855500/29855495/e638bc07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29860000/29855500/29855495/d98da783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/30000000/29860000/29855500/29855495/aec4bc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming apt -2 Bedroom -Close to Beach/Sleeps 6 [](https://www.expedia.ca/Ipswich-Hotels-Charming-Apt-2-Bedroom-Close-To-BeachSleeps-6.h29855495.Hotel-Information) Ipswich 9.2/10 Wonderful (23 reviews) "Perfect for our family for a 1 night stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bailey S. CA $138 CA $309 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Ipswich-Hotels-Charming-Apt-2-Bedroom-Close-To-BeachSleeps-6.h29855495.Hotel-Information) ![Smart TV, video games, DVD player, books](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/517dec7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/7835b4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/05c9d343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/e675061f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes! [](https://www.expedia.ca/Hampton-Hotels-Premier.h112074082.Hotel-Information) Hampton Beach 10/10 Exceptional (12 reviews) "We had a great stay. The house is beautiful, short walk to the beach, and has plenty of parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura C. CA $281 CA $561 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Hampton-Hotels-Premier.h112074082.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=2026-01-31&endDate=2026-02-01®ionId=8008&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Gloucester Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Packages - Other - More ways to book - [Cheap Hotels in Annisquam ](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Cheap-Hotels.0-n553248635975257320-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Annisquam ](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Historic-Hotel.0-n553248635975257320-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Annisquam ](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Honeymoon-Hotels.0-n553248635975257320-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Annisquam ](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Pet-Friendly-Hotel.0-n553248635975257320-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Boston ](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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