Title: Book the Best Western Shore of Maryland WINERY Hotels in 2026 | 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) ![Ego Alley](https://images.trvl-media.com/place/553248635919228117/0d4dbc48-9997-4c5e-a132-1c0595902ce6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Western Shore of Maryland, MD from CA $132 - ![](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 Western Shore of Maryland Winery Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6057468&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Western Shore of Maryland hotels with winery ![Bar (on property)](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ff957644.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) ![Lobby](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/61316540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ca9c2666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) Bel Air 9.2/10 Wonderful (228) "Friendly staff, clean hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $123 CA $138 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/aabb28e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/fa54a5ac.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/2000000/1170000/1160800/1160798/9ee94703.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 [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) Annapolis 8.8/10 Excellent (179) "Nice staff, clean room, comfortable bed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayne CA $116 CA $132 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/f058e662.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) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/2279c753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/cf0869c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Bel Air [](https://www.expedia.ca/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) Bel Air 8.8/10 Excellent (437) "We had a great stay here! The room was clean and the beds were very comfortable, even the pull out sofa. The breakfast buffet had a good number of options. All of the staff we encountered were so friendly and helpful. My kids enjoyed the pool, and the hot tub was the cleanest - I even went in! We would stay here again the next time we are in the area! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly CA $126 CA $141 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/50c62e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/4366a05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/48533afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/46cacd12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Baltimore Inner Harbor [](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.Hotel-Information) Downtown West 8.4/10 Very good (1871) "Room was very nice with great view." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $151 CA $178 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.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) ![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/1000000/30000/28400/28314/9aa828c1.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) ### Hotel Revival Baltimore [](https://www.expedia.ca/Baltimore-Hotels-Hotel-Revival-Baltimore.h28314.Hotel-Information) Mount Vernon 9.4/10 Exceptional (1002) "Our room was quite large and beautiful. The hotel is in a great location. I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathleen CA $174 CA $224 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Baltimore-Hotels-Hotel-Revival-Baltimore.h28314.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) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/7800/7741/cddb6999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7800/7741/b744745d.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) ### Holiday Inn Express Towson - Baltimore North by IHG [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Towson-Baltimore-North.h7741.Hotel-Information) Towson 9.0/10 Wonderful (1073) "Friendly and helpful staff and great beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Serafina CA $121 CA $141 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Towson-Baltimore-North.h7741.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/414bd0fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/a75bb6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/10bef897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/488be20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. [](https://www.expedia.ca/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information) Owings 10/10 Exceptional (48) "We love this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan K. CA $174 CA $375 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8c6112e0.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) ### Waterfront Oasis of Annapolis Star [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) Annapolis 10/10 Exceptional (81) "Owners were great hosts. Loved this property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $285 CA $570 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/w905h683x59y0-876363d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/8ef47f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/a6453963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/w1024h572x0y56-a1edfb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Modern Micro Apt in the Heart of Fells Point! [](https://www.expedia.ca/Baltimore-Hotels-Cozy-Modern-Micro-Apt-In-The-Heart-Of-Fells-Point.h83828255.Hotel-Information) Fells Point 9.0/10 Wonderful (30) "We had such a great stay at the property. Everything was clean and welcoming. It was the perfect little place/space for my wife my 3 yr old son and myself. The street parking in the area was also good. We were able to find a spot right around the corner. The location of the property in relation to a lot of the sites in Fells Point was perfect as well. Everything 5 stars we would definitely recommend and We would definitely book again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan S. CA $143 CA $341 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Baltimore-Hotels-Cozy-Modern-Micro-Apt-In-The-Heart-Of-Fells-Point.h83828255.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/62000000/61640000/61636900/61636832/3d050faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61640000/61636900/61636832/d87e70b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61640000/61636900/61636832/w1179h1561x0y0-8b0740e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/62000000/61640000/61636900/61636832/d249eb20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Farm Home Near I83\. Minutes from wedding venues! Fire pit, hiking trails! [](https://www.expedia.ca/White-Hall-Hotels-Cozy-Apartment-On-A-Private-Horse-Farm.h61636832.Hotel-Information) White Hall 10/10 Exceptional (36) "We chose this property since it is located reasonably close to our family (grandchildren) and to the Manor Tavern and Oregon Grille our favorite restaurants in the area. Beautiful, private area in Maryland horse country!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald F. CA $193 CA $392 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/White-Hall-Hotels-Cozy-Apartment-On-A-Private-Horse-Farm.h61636832.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=2025-12-26&endDate=2025-12-27®ionId=6057468&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Western Shore of Maryland Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in Hampton ](https://www.expedia.ca/5Star-Hampton-Baltimore-Hotels.s50-n553248635975874015-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Parkville ](https://www.expedia.ca/5Star-Parkville-Hotels.s50-0-d143755.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Baldwin ](https://www.expedia.ca/Baldwin-Hotels-Cheap-Hotels.0-0-d6338535-tCheapHotels.Travel-Guide-Filter-Hotels) - [B&B in Baltimore County ](https://www.expedia.ca/Baltimore-County-Bed-And-Breakfast.d553248635083904998-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Baltimore County ](https://www.expedia.ca/Baltimore-County-Castles.d553248635083904998-aaCastles.Travel-Guide-Accommodation) - 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