Title: Book the Best Western Shore of Maryland WINERY Hotels in 2025 | Expedia.ca [Western Shore of Maryland Travel Guide](https://expedia.ca/Western-Shore-Of-Maryland.dx6057468)[Hotels in Western Shore of Maryland](https://expedia.ca/Western-Shore-Of-Maryland-Hotels.d6057468.Travel-Guide-Hotels)[Vacation Rentals in Western Shore of Maryland](https://expedia.ca/Western-Shore-Of-Maryland-Vacation-Rentals.d6057468.Travel-Guide-VacationRentals)[Flights to Western Shore of Maryland](https://expedia.ca/Cheap-Flights-To-Western-Shore-Of-Maryland.d6057468.Travel-Guide-Flights)[Western Shore of Maryland Car Rentals](https://expedia.ca/Car-Rentals-In-Western-Shore-Of-Maryland.d6057468.Car-Rental-Guide)[Western Shore of Maryland Vacation Packages](https://expedia.ca/Western-Shore-Of-Maryland.d6057468.Destination-Travel-Guides) ![Boordy Vineyards](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/27000/27035-Boordy-Vineyards.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Western Shore of Maryland, 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 Western Shore of Maryland Winery Hotels Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Western Shore of Maryland Winery Hotels ![Breakfast, lunch, dinner served; alfresco dining](https://images.trvl-media.com/lodging/1000000/30000/27100/27044/486f024b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gastropub](https://images.trvl-media.com/lodging/1000000/30000/27100/27044/112a56f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/30000/27100/27044/4ae92812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Self-serve breakfast for a fee on weekdays](https://images.trvl-media.com/lodging/1000000/30000/27100/27044/0cba4488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Merriweather Lakehouse, Autograph Collection Town Center 9.2/10 Wonderful (332) "Great hotel" CA $304 CA $344 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Baltimore-Hotels-Merriweather-Lakehouse.h27044.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/20000000/19660000/19654100/19654052/624fc091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/20000000/19660000/19654100/19654052/6ddd65b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/20000000/19660000/19654100/19654052/f2532c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19660000/19654100/19654052/cf67b98f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton York York 9.2/10 Wonderful (866) "Excellent stay. Very friendly staff!" CA $129 CA $143 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/York-Hotels-Tru-By-Hilton-York.h19654052.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (825) "Friendly staff, clean room, convenient location. " CA $160 CA $177 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/10000/7800/7741/4c06ee0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7800/7741/18902aaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7800/7741/c1f25fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/7800/7741/62193e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Towson - Baltimore North by IHG Towson 9.0/10 Wonderful (1034) "The staff was very helpful and everything was very clean. The food was very good and we really enjoyed the exercise room" CA $147 CA $171 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Towson-Baltimore-North.h7741.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/2000000/1170000/1160800/1160798/38f7156f.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/1a3cf5be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Annapolis by IHG Annapolis 8.8/10 Excellent (133) "Nice area, clean, comfortable, pleasant staff" CA $135 CA $154 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/a4c59418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/71bdd057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1f3f9838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/74da44e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air Bel Air 9.2/10 Wonderful (215) "The staff was amazing" CA $164 CA $183 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/996623d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/f058e662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/f0204afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/418e7e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Bel Air Bel Air 8.8/10 Excellent (420) "Staff were very welcoming and helpful!" CA $166 CA $186 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/3a2b6d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/5b665845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/5cebc14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/95c3065a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Revival Baltimore Mount Vernon 9.4/10 Exceptional (1005) "Great stay! Clean rooms, friendly staff, and convenient location." CA $150 CA $196 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Baltimore-Hotels-Hotel-Revival-Baltimore.h28314.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/12e4e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/114f1de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/5c9fbfa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Baltimore North, MD Rossville 7.2/10 Good (1000) "I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10... CA $136 CA $157 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93370000/93366800/93366726/w1350h891x0y4-5f6b830b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/94000000/93370000/93366800/93366726/955d3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93370000/93366800/93366726/dcf0e909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/94000000/93370000/93366800/93366726/a3055d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Houseboat: Breathtaking Skyline 360 Views Inner Harbor 10/10 Exceptional (18) "Quieter and nicer than most luxury hotels. Awesome stay and experience." CA $439 CA $944 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Baltimore-Hotels-Luxe-Houseboat-Breathtaking-Skyline-360-Views.h93366726.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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