Title: Book the Best Western Maryland WINERY Hotels in 2025 | Expedia.ca [Western Maryland Travel Guide](https://expedia.ca/Western-Maryland.dx6057473)[Hotels in Western Maryland](https://expedia.ca/Western-Maryland-Hotels.d6057473.Travel-Guide-Hotels)[Vacation Rentals in Western Maryland](https://expedia.ca/Western-Maryland-Vacation-Rentals.d6057473.Travel-Guide-VacationRentals)[Flights to Western Maryland](https://expedia.ca/Cheap-Flights-To-Western-Maryland.d6057473.Travel-Guide-Flights)[Things to do in Western Maryland](https://expedia.ca/Things-To-Do-In-Western-Maryland.d6057473.Travel-Guide-Activities)[Western Maryland Car Rentals](https://expedia.ca/Car-Rentals-In-Western-Maryland.d6057473.Car-Rental-Guide)[Western Maryland Vacation Packages](https://expedia.ca/Western-Maryland.d6057473.Destination-Travel-Guides) ![Carrol Creek Linear Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253245-Maryland.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Western Maryland - ![](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 Maryland Winery Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6057473&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6057473&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6057473&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6057473&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Western Maryland Winery Hotels ![Lobby](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/1a1740a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/acf48b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/e87eadf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/d43d754c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Cumberland Cumberland 9.6/10 Exceptional (621) "Staff was friendly and was very helpful during the stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $189 CA $215 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Cumberland-Hotels-Hampton-Inn-Cumberland.h22789141.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/f92e85d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/79c6bb79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 King Bed Corner Room w/ Sofabed Nonsmoking](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/80cf47d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/e9944ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Frederick Frederick 8.2/10 Very good (1002) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathie CA $139 CA $154 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Frederick-Hotels-Hampton-Inn-Frederick.h21470.Hotel-Information) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/90000/84900/84829/5e8caf12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/90000/84900/84829/ebbdee0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/90000/84900/84829/4db1b608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/90000/84900/84829/6b5cf394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suburban Studios LaVale-Cumberland Cumberland 7.0/10 Good (663) "Woman that checked us in was great and friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremy CA $106 CA $121 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Cumberland-Hotels-Rodeway-Inn.h84829.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/9c1d9621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/1a9ef301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/3c5b5f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️ Secluded 1940s Romantic Tiny House on the River Shepherdstown 10/10 Exceptional (63) "We truly loved this location and definitely will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Astrid CA $55 CA $147 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90200000/90198000/90197904/89453f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90200000/90198000/90197904/4ccd7d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90200000/90198000/90197904/5380b7ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90200000/90198000/90197904/d9e62de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly) Frederick 10/10 Exceptional (60) "We thoroughly enjoyed our stay in Frederick. The cottage was comfortable and an easy walk to shops, parks and restaurants. We would definitely stay here for our next trip to Frederick. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen B. CA $125 CA $316 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Frederick-Hotels-The-Cottage-On-Dill.h90197904.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/cf8a1df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/335684a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/a62a4c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/00037a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cabin in the Woods with River Access Shepherdstown 9.6/10 Exceptional (38) "Loved the cabin and seclusion. Would come back for sure. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark S. CA $175 CA $356 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Shepherdstown-Hotels-Charming-Cabin-In-The-Woods-With-River-Access.h100779583.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/8720e416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/c7101f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/16c3621f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/d3c1582f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek. Berkeley Springs 9.8/10 Exceptional (288) "It was a great time, easy check in and out! Grill and hot tub were great, and there was an amazing view of the stars." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julian B. CA $140 CA $445 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Private-Getaway-W-Hot-Tub.h27132250.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/55851da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/286a3bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/53e738c1.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/34000000/33420000/33415400/33415316/c515c5dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803 Hagerstown 10/10 Exceptional (122) "The space and location are absolutely wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $145 CA $231 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hagerstown-Hotels-Springhouse-1803-Unique-Historic-Home.h33415316.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/87000000/86150000/86144100/86144049/57606b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/87000000/86150000/86144100/86144049/09a8e35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/87000000/86150000/86144100/86144049/2a94ac79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/87000000/86150000/86144100/86144049/ae31e59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC Brunswick 9.8/10 Exceptional (48) "Nice place. We loved all the thoughtful touches that Kim has put into the place. My sister's and I stayed in the "Cozy" cottage.Thanks for a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) June H. CA $113 CA $224 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brunswick-Hotels-Cozy-Getaway-Near-Harpers-Ferry.h86144049.Hotel-Information) ![](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/0ed0ba48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/afee337d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/7d8e3efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/7c41d2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT. Downtown Frederick 9.4/10 Exceptional (117) "We enjoyed our stay here. It was a great location, well restored, and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meagan P. CA $171 CA $408 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Frederick-Hotels-RETREAT-On-The-CREEK-Businees-Travelor-Or-Weekend-Getaway-HISTORIC-DISTRICT.h21298018.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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[Mid-Atlantic Vacation Rentals](https://www.expedia.ca/Mid-Atlantic-Vacation-Rentals.d6209850.Travel-Guide-VacationRentals) - [Things to do in Assateague Island](https://www.expedia.ca/Things-To-Do-In-Assateague-Island.d553248635976198150.Travel-Guide-Activities) - [Things to do in Chesapeake Bay](https://www.expedia.ca/Things-To-Do-In-Chesapeake-Bay.d6056980.Travel-Guide-Activities) - [Things to do in Virginias](https://www.expedia.ca/Things-To-Do-In-Virginias.d6209940.Travel-Guide-Activities) - [Book Winery Hotels in Western Maryland on Expedia.com](https://www.expedia.com/Western-Maryland-Hotels-Winery-Hotel.0-0-d6057473-tWineryHotel.Travel-Guide-Filter-Hotels)