Title: 5 Stars Hotels in Oakland, Maryland - Find Cheap Oakland Hotels With 5 Stars | Expedia.ca [Oakland Travel Guide](https://expedia.ca/Oakland.dx9160)[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)[Flights to Oakland](https://expedia.ca/Cheap-Flights-To-Oakland.d9160.Travel-Guide-Flights)[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 # 5 Stars Hotels in Oakland, 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 Oakland 5 Star Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland 5 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/1a59f6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Hot Tub | Bathroom](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/3215a99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/b214397c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Hot Tub | Private kitchen](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/183017ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Preston on the Lake 5 Bedroom House Oakland [](https://www.expedia.ca/Cumberland-Hotels-Preston-On-The-Lake-5-Bedroom-House.h32721047.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oakland-Hotels.s50-0-d9160.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oakland-Hotels.s50-0-d9160.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland. ![Loft of Luxury](https://images.trvl-media.com/lodging/78000000/77820000/77817200/77817107/91474100_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Loft of Luxury Oakland [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=77817107&PinnedHotelID=77817107&HadPinnedHotel=true®ionId=9160) [](https://expedia.ca/Oakland-Hotels-Loft-Of-Luxury.h77817107.Hotel-Information) ![Bear Hollow Lodge](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/a709d25a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Bear Hollow Lodge 20590 GARRETT HWY, Oakland, MD [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=75970245&PinnedHotelID=75970245&HadPinnedHotel=true®ionId=9160) [](https://expedia.ca/Oakland-Hotels-Bear-Hollow-Lodge.h75970245.Hotel-Information) ![Strawberry Fields](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011499/72883e89_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Strawberry Fields 10 ROMAN RIDGE RD #22A, Oakland, MD [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=76011499&PinnedHotelID=76011499&HadPinnedHotel=true®ionId=9160) [](https://expedia.ca/Oakland-Hotels-Strawberry-Fields.h76011499.Hotel-Information) Still don't see what you're looking for? [See all properties in Oakland.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Oakland Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors. [See all hotels in Oakland](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&adults=2®ionId=9160) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=900&h=675&p=1&q=high) Photo by KM Moore ## Top Oakland Hotel Reviews ## Find out more about Oakland ## Five Star Hotels in Oakland There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Oakland so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Oakland and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Oakland Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Oakland The results are in, and Oakland 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Oakland! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Oakland today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Oakland? > How much you pay for a 5-star hotel in Oakland depends on factors like when you plan to travel and the length of your vacation. A top tip for bagging an awesome deal? Use our pricing filters to compare the available hotels for your selected dates. > > > > - Search for the lowest price per night ### What makes a hotel 5 stars in Oakland? > In Oakland, a hotel is required to offer a certain amount of top-notch amenities to earn a 5-star rating. These may include on-site gyms, saunas and spas, gourmet restaurants, premium bedding, complimentary luxury toiletries and more. What also sets 5-star hotels apart is their superior standard of service. You can look forward to things like nightly turn-down services, concierge services and in-room massages. Some may also offer extra touches like welcome gifts. ### Are there any 5-star all-inclusive resorts in Oakland? > Use our filter tool to find a high-end getaway in Oakland where most of what you need is included. From there, narrow down your results for accommodations that have 5 stars and are categorized as "All inclusive." The main thing on the to-do list at these stays? 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