Title: Book the Best Oakland LUXURY Hotels - Upscale Hotels in Oakland, MD | 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) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KM Moore # Find luxury 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 Luxury Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-31&endDate=2025-11-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-01&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Oakland Luxury Hotels ## Top Oakland Hotel Reviews ## Frequently asked questions ### Are you searching for a great accommodation for your luxury holiday in Oakland? > Use Expedia to arrange your flight to Morgantown, WV (MGW-Morgantown Municipal) airport or Elkins, WV (EKN-Randolph County) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Oakland has to offer. Known for its riverfront, Oakland also has some interesting things to see and do including Deep Creek Lake, so you may want to take in the local sights during your visit. ### When can I expect good weather in Oakland? > Planning for the weather is an important factor for making your trip to Oakland a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Oakland are January, December, February, and May, with each month seeing an average of 31 inches of snowfall. ### What's there to see and do in Oakland? > Enjoy all that Oakland has to offer when you visit Deep Creek Lake, Herrington Manor State Park, and Swallow Falls State Park. 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