Title: Book the Best Annapolis WINERY Hotels in 2025 | Expedia.ca [Annapolis Travel Guide](https://expedia.ca/Annapolis.dx6034082)[Hotels in Annapolis](https://expedia.ca/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)[Vacation Rentals in Annapolis](https://expedia.ca/Annapolis-Vacation-Rentals.d6034082.Travel-Guide-VacationRentals)[Flights to Annapolis](https://expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Things to do in Annapolis](https://expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)[Annapolis Car Rentals](https://expedia.ca/Car-Rentals-In-Annapolis.d6034082.Car-Rental-Guide)[Annapolis Vacation Packages](https://expedia.ca/Annapolis.d6034082.Destination-Travel-Guides) ![Annapolis](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253221-Annapolis.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Annapolis, MD ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Annapolis Winery Hotels Tonight [Sep 22 - Sep 23](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-09-22&endDate=2025-09-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-09-23&endDate=2025-09-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Annapolis Winery Hotels ## Top Annapolis Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Anne Arundel County](https://www.expedia.ca/Anne-Arundel-County-Bed-And-Breakfast.d553248635083910990-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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