Title: Book the Best Oakland WINERY Hotels in 2025 | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d9160.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d9160.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d9160.Car-Rental-Guide)[Oakland Vacation Packages](https://expedia.ca/Oakland.d9160.Destination-Travel-Guides) ![Waterfall at Swallow Falls](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jenn Charbonneau # Find Winery Hotels in Oakland, MD - ![](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 Oakland Winery Hotels Tonight [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-23&endDate=2025-11-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-24&endDate=2025-11-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/d68aefb9.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) ![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/116000000/115190000/115182200/115182127/067bcc9c.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. 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 $140 CA $498 total includes taxes & fees Dec 8 - Dec 9 [](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/77000000/76390000/76383500/76383432/a57c8041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383432/d2fd842a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383432/11dcc5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383432/98a26ba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suites at Silver Tree: A118 Studio Standard View Oakland 10/10 Exceptional (1) "Great place for a quick getaway ski trip to Wisp" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William A. CA $290 CA $374 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A118-Studio-Standard-View.h76383432.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477797/65a9d2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477797/0f35f005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477797/d3ffd798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477797/73f8418b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 208 King Room ADA Accessible Oakland 10/10 Exceptional (4) "I enjoyed the still of the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shundrey CA $328 CA $424 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-208-King-Room-ADA-Accessible.h106477797.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477815/8c3f55d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477815/a0cf332a.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/107000000/106480000/106477900/106477815/b920f00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477815/f2f0dd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 215 Standard Double Queen Room Oakland 10/10 Exceptional (2) "It was very clean and the workers were so kind and was the perfect little get away for my family! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $335 CA $431 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-215-Standard-Double-Queen-Room.h106477815.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477803/ec954146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477803/44bc4f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477803/8a834c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477803/36fa0af3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 210 Standard Double Queen Fireplace Room Oakland 10/10 Exceptional (9) "What a wonderful place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edna S. CA $341 CA $422 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-210-Standard-Double-Queen-Fireplace-Room.h106477803.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477813/5eb5f187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477813/979b0555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477813/2f0d90c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477813/2b368471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 214 Standard Double Queen Fireplace Room Oakland 9.0/10 Wonderful (2) "Well located for our trip. We wanted to explore the area and things to do in anticipation of our whole family meeting in the Deep Creek area. Near excellent coffee (Trader), modest bakery and dining options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $341 CA $440 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-214-Standard-Double-Queen-Fireplace-Room.h106477813.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477817/fa3c6109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477817/51726c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477817/796e7ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477900/106477817/899623d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 216 Lakeside Double Queen Room Oakland 10/10 Exceptional (1) "Such a cute place on the lake! The common areas were great and the bar looked cool! The room was so cozy and comfortable - loved all the branded mugs and wine glasses! Property was perfect and had so many cute places to relax" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gillian W. CA $351 CA $454 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-216-Lakeside-Double-Queen-Room.h106477817.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477775/5f21fb8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477775/8351506c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477775/1a68ea23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477775/9fcee11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 201 Poolside Double Queen Fireplace Room Oakland 10/10 Exceptional (5) "Great place, great amenities!! We will definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica C. CA $360 CA $464 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-201-Poolside-Double-Queen-Fireplace-Room.h106477775.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477781/e175550b.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/107000000/106480000/106477800/106477781/aec66002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477781/b71f9dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/107000000/106480000/106477800/106477781/428a6bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cove Creek Lodge: 203 Poolside Double Queen Room Oakland 10/10 Exceptional (4) "Check in a breeze fun trip thanks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike O. CA $350 CA $451 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Cove-Creek-Lodge-203-Poolside-Double-Queen-Room.h106477781.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/67273f74_edited_ee80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/b175e07a_edited_6725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/16a77489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/8e09a628_edited_6866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Will O' The Wisp: 103A Efficiency/One Bath Oakland 9.6/10 Exceptional (8) "Rekaxing, restful, beautiful views" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald D. CA $343 CA $442 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-103A-EfficiencyOne-Bath.h76515341.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=2025-12-07&endDate=2025-12-08®ionId=9160&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_9160) ## Top Oakland Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in Paradise Point](https://www.expedia.ca/2Star-Paradise-Point-Oakland-Hotels.s20-n553248635976481309-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Mountainside](https://www.expedia.ca/5Star-Mountainside-Oakland-Hotels.s50-n553248635976481730-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sunplace](https://www.expedia.ca/5Star-Sunplace-McHenry-Hotels.s50-n553248635976468730-0.Travel-Guide-Filter-Hotels) - 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[Flights from Cleveland (CLE) to Oakland (ODM)](https://www.expedia.ca/lp/flights/cle/odm/cleveland-to-oakland) - [Flights from New York (JFK) to Oakland (ODM)](https://www.expedia.ca/lp/flights/jfk/odm/new-york-to-oakland) - [Deep Creek Lake](https://www.expedia.ca/Deep-Creek-Lake-Maryland.d553248635959734861.Vacation-Attraction) - [Friendsville Vacations](https://www.expedia.ca/Friendsville.d6338432.Destination-Travel-Guides) - [Funland](https://www.expedia.ca/Funland-McHenry.d553248621532660290.Vacation-Attraction) - [Visit Thayerville](https://www.expedia.ca/Thayerville.dx553248635975871934) - [Wisp Resort](https://www.expedia.ca/Wisp-Resort-McHenry.d6091719.Vacation-Attraction) - [Car rental McHenry](https://www.expedia.ca/Car-Rentals-In-McHenry.d131592.Car-Rental-Guide) - [Book Winery Hotels in Oakland on Expedia.com](https://www.expedia.com/Oakland-Hotels-Winery-Hotel.0-0-d9160-tWineryHotel.Travel-Guide-Filter-Hotels)