Title: Book the Best Cumberland WINERY Hotels in 2026 | Expedia.ca [Hotels in Cumberland](https://expedia.ca/Cumberland-Hotels.d6057474.Travel-Guide-Hotels)[Vacation Rentals in Cumberland](https://expedia.ca/Cumberland-Vacation-Rentals.d6057474.Travel-Guide-VacationRentals)[Things to do in Cumberland](https://expedia.ca/Things-To-Do-In-Cumberland.d6057474.Travel-Guide-Activities)[Cumberland Car Rentals](https://expedia.ca/Car-Rentals-In-Cumberland.d6057474.Car-Rental-Guide)[Cumberland Vacation Packages](https://expedia.ca/Cumberland.d6057474.Destination-Travel-Guides) ![Great trains in Cumberland. Rudd the rail to Frostberg. ](https://images.trvl-media.com/place/6057474/7b8cb179-869f-48b5-a727-cfc5d2957e77.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Sig # Find Winery Hotels in Cumberland, MD from CA $104 - ![](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 Cumberland Winery Hotels Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=6057474&startDate=2025-12-29&endDate=2025-12-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=6057474&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6057474&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6057474&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cumberland hotels with winery ![Lobby](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/1a1740a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/9161add0.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) ![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) ### Hampton Inn Cumberland [](https://www.expedia.ca/Cumberland-Hotels-Hampton-Inn-Cumberland.h22789141.Hotel-Information) Cumberland 9.6/10 Exceptional (638) "Great stay! Friendly staff at check in, clean rooms, the bed was so comfortable. A great breakfast. Overall enjoyable stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $149 CA $170 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Cumberland-Hotels-Hampton-Inn-Cumberland.h22789141.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/90000/84900/84829/c51bc8c9.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) ![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) ### Suburban Studios LaVale-Cumberland [](https://www.expedia.ca/Cumberland-Hotels-Rodeway-Inn.h84829.Hotel-Information) Cumberland 7.0/10 Good (676) "Very nice & clean Nice rooms && quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $91 CA $104 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Cumberland-Hotels-Rodeway-Inn.h84829.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147267/accbdaf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147267/ea1329a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147267/073feadb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147267/380181b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BIG D's POND & North Branch of the Potomac river Camping. [](https://www.expedia.ca/Cumberland-Hotels-BIG-Ds-POND-North-Branch-Of-The-Potomac-River-Camping.h39147267.Hotel-Information) Cumberland 10/10 Exceptional (3) "Big D'S Pond is beautiful and the owner, is very kind and helpful. We had an amazing time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary G. CA $85 CA $155 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Cumberland-Hotels-BIG-Ds-POND-North-Branch-Of-The-Potomac-River-Camping.h39147267.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/d68aefb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/4e8ed583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/80e692ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/067bcc9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats. [](https://www.expedia.ca/Oakland-Hotels-Lake-Views-HOT-TUB-Central-Location-Walk-To-Coffee.h115182127.Hotel-Information) Oakland 10/10 Exceptional (4) "The place was so clean and fully stocked. We had a wonderful stay. Five stars!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori S. CA $492 CA $895 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Oakland-Hotels-Lake-Views-HOT-TUB-Central-Location-Walk-To-Coffee.h115182127.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383474/c79f355f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383474/8b8bb18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383474/adbc61ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383474/0376cce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suites at Silver Tree: A210 Studio Standard View [](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A210-Studio-Standard-View.h76383474.Hotel-Information) Oakland 10/10 Exceptional (2) "The property was absolutely beautiful! Right on the lake with amazing views! Secluded but close shops and restaurants! The room was very clean and welcoming! The only downside is the parking. When it’s dinner time, the hotel guests have to fight for parking spaces with the restaurant patrons. Other than that, we had an amazing stay. We’ll definitely be staying there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David H. CA $283 CA $364 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A210-Studio-Standard-View.h76383474.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/87ad376f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/04faed71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/edca1a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/4cd29209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Farm, Near Lake, 10 Acres, Newly Renovated [](https://www.expedia.ca/Swanton-Hotels-Historic-Farm.h48604478.Hotel-Information) Swanton 9.8/10 Exceptional (10) "The Historic Farm property was beautiful! Our family enjoyed fishing at the pond and biking in and around the property. We hiked and swam in the nearby State Parks. The bedrooms were spacious and the king sized beds comfortable. It was great to have meals with the whole family around the large dining room table. The ice machine in the cozy kitchen was an added bonus." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl W. CA $2,256 CA $3,203 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Swanton-Hotels-Historic-Farm.h48604478.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/8e6e3a46_edited_eb2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/663df6f1_edited_80c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/1763dd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/4029cfb4_edited_a4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Will O' The Wisp: 107B One Bedroom/One Bath [](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-107B-One-BedroomOne-Bath.h100856128.Hotel-Information) Mountainside 10/10 Exceptional (2) "Great place to visit. Hope to come back next year" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy S. CA $360 CA $458 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-107B-One-BedroomOne-Bath.h100856128.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477790/48228227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477790/92c0e93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477790/b8a317b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477790/cb080bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 206 Standard King Room [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-206-Standard-King-Room.h106477790.Hotel-Information) Oakland CA $317 CA $406 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-206-Standard-King-Room.h106477790.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477799/4a55322d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477799/3ab7938e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477799/971d8ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477799/90397554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 209 Standard Double Queen Room [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-209-Standard-Double-Queen-Room.h106477799.Hotel-Information) Oakland CA $324 CA $416 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-209-Standard-Double-Queen-Room.h106477799.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/1f9afee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/a46aee5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/be49f9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console, DVD player](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/da0ce863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger! [](https://www.expedia.ca/Oakland-Hotels-Unwind-At-Jamesons-Cabin-Pet-Friendly.h91123713.Hotel-Information) Oakland 10/10 Exceptional (34) "Great property, loved our stay here! We will definitely stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawnnelle H. CA $377 CA $1,044 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Oakland-Hotels-Unwind-At-Jamesons-Cabin-Pet-Friendly.h91123713.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=2026-01-12&endDate=2026-01-13®ionId=6057474&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Cumberland Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Westernport ](https://www.expedia.ca/4Star-Westernport-Hotels.s40-0-d3000440935.Travel-Guide-Filter-Hotels) - [Hotels near Allegany County Fairgrounds ](https://www.expedia.ca/Allegany-County-Fairgrounds-Hotels.0-l553248635975883245-0.Travel-Guide-Filter-Hotels) - [Farmstay in Barton ](https://www.expedia.ca/Barton-Agritourism.d553248626204850781-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Barton ](https://www.expedia.ca/Barton-Apart-Hotels.d553248626204850781-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Barton ](https://www.expedia.ca/Barton-Bed-And-Breakfast.d553248626204850781-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Barton Hotels ](https://www.expedia.ca/Barton-Hotels.d553248626204850781.Travel-Guide-Hotels) - 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