Title: Book the Best Hotels with POOL in Oakland 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) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KM Moore # Find Hotels with a Pool in Oakland, MD ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Hotels with a Pool Tonight [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-09-29&endDate=2025-09-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-09-30&endDate=2025-10-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Hotels with a Pool ## Top Oakland Hotel Reviews ## Frequently asked questions ### What's it like visiting Oakland? > If taking it easy by the pool is your idea of the perfect getaway, you may want to consider luxurious Oakland, which has 29 places to stay with pools. During your trip, you can explore sights such as Deep Creek Lake, and then relax and unwind poolside at one of the accommodations in Oakland that travelers like for their pools. ### What are some accommodations with pools in Oakland? > [Baja Motel](https://www.expedia.ca/Oakland-Hotels-Riverside-Suites.h99839480.Hotel-Information): Vacation home, 14-minute walk from Deep Creek Lake. Features kitchens, a pool, and Smart TVs. [The Garrett Inn](https://www.expedia.ca/Cumberland-Hotels-The-Garrett-Inn.h14910340.Hotel-Information): Vacation home, 5-minute walk from Deep Creek Lake. Provides kitchens, a communal pool, and televisions. [New: Lakefront Luxury Home with Private Indoor Heated Pool!](https://www.expedia.ca/Oakland-Hotels-New-Lakefront-Luxury-Home-With-Private-Indoor-Heated-Pool.h100201414.Hotel-Information): Cottage, 15-minute walk from Deep Creek Lake. Features complimentary wireless internet access, a communal pool, and kitchens. [Amazing Central Location! Lakefront! Hot tub/dock!](https://www.expedia.ca/Oakland-Hotels-Amazing-Central-Location-Lakefront-Hot-Tubdock.h62988840.Hotel-Information): Vacation home, 6-minute walk from Deep Creek Lake. Offers complimentary wireless internet access, an indoor pool, and kitchens. ### How many pool hotels will I be able to find in Oakland? > Expedia's 29 hotels in Oakland give you a great choice for your poolside getaway. ### What is there to see and do in Oakland? > Explore places like Deep Creek Lake while you're in Oakland. Spend some time experiencing the great outdoors at Youghiogheny River and Oakland Dog Park. Take in the natural beauty of Oakland with the lakeside setting and riverfront. ### When is the best time to book a hotel with a pool in Oakland? > Taking into account the local weather in Oakland can help you maximize your time at the pool during your trip. 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. 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