Title: Book the Best West Annapolis WINERY Hotels in 2025 | Expedia.ca [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)[West Annapolis Car Rentals](https://expedia.ca/Car-Rentals-In-West-Annapolis.d553248635976472135.Car-Rental-Guide)[West Annapolis Vacations](https://expedia.ca/West-Annapolis.d553248635976472135.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/43ecd26a78c4814e08d2d9650817b177.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Eric Mondres # Find Winery Hotels in West Annapolis, MD from CA $139 ![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 West Annapolis Winery Hotels Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976472135&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976472135&startDate=2025-10-09&endDate=2025-10-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976472135&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976472135&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top West Annapolis Winery Hotels ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (114) "Great INN super nice staff" CA $264 CA $345 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9088c5e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/1a3cf5be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/0914d7ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Annapolis by IHG Annapolis 8.8/10 Excellent (136) "Nice area, clean, comfortable, pleasant staff" CA $135 CA $154 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Mobility Accessible (Shower) | Bathroom](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/ce6b0c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/2f8ab1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/c97041ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garner Hotel Glen Burnie BWI Airport Area by IHG Glen Burnie 6.6/10 (1005) "Very clean and the staff were very friendly!" CA $122 CA $139 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/cc3df3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/7bad8500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Pet-Friendly Stay - Near Bay & Beaches. Annapolis 10/10 Exceptional (5) "The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here." CA $393 CA $869 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/93cefa30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/990d9aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/0a7737a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8b5db833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach Arundel on the Bay 10/10 Exceptional (10) "Very clean - well equipped - perfect for our relaxing weekend." CA $301 CA $711 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/f520f52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0fab08c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Oasis of Annapolis Star Annapolis 10/10 Exceptional (79) "Very nice place to say for a getaway weekend. Great homeowners as well, 10/10." CA $376 CA $690 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/ba6b073a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/5acb80c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis Historic District 10/10 Exceptional (71) "The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay" CA $166 CA $434 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/ccf7fb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/w1170h778x0y0-525d5ef7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/bf64d3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/a0026e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Comfort, Annapolis. Annapolis 10/10 Exceptional (17) "Great place centrally located to amenities and Navy stadium. We booked an overnite with family to attend a graduation dinner nearby. " CA $321 CA $736 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Annapolis-Hotels-Chesapeake-Comfort.h57359083.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=2025-10-22&endDate=2025-10-23®ionId=553248635976472135&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top West Annapolis Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Annapolis Hotels](https://www.expedia.ca/Annapolis-Hotels.d6034082.Travel-Guide-Hotels) - [B&B in Anne Arundel County](https://www.expedia.ca/Anne-Arundel-County-Bed-And-Breakfast.d553248635083910990-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Anne Arundel County](https://www.expedia.ca/Anne-Arundel-County-Motels.d553248635083910990-aaMotels.Travel-Guide-Accommodation) - [Honeymoon Resorts and in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - 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