Oakland Vacation Rentals
Compare 32 vacation rentals.
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Oakland's visitors know that time slows down during a walk past the main street's historic sights and shops, and the magic lingers through a drive out to nearby Deep Creek Lake, where outdoor adventure resides year-round. Book one of our vacation rentals in Oakland to experience Maryland's forests and mountains in every season, and stick around for the town's quaint charms.
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Yes, 32 of our Oakland homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).
Browse dog-friendly homes >Yes. 87 of our Oakland vacation rentals have internet access, so you can stay connected throughout your trip.
Browse homes with internet access >Absolutely. Our local Oakland team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.
Learn more about Vacasa Premium Clean >Whether you're out shopping for antiques or ordering an old-fashioned milkshake at Englander's, your stay at one of our Oakland vacation rentals means a peek into a simpler time. Join locals at the Oakland Golf Club for a round on a championship course, or make your way down the Glades or 88 Bridge walking and biking paths for some scenic exercise. A day's drive brings you to Baltimore or Pittsburgh, while neighboring towns such as McHenry and Swanton are just a short drive away.
Oakland sits in the heart of Garrett County's woods, and guests at our Oakland rentals encounter Deep Creek adventure in any season. A 14-mile drive brings you to Wisp's winter ski slopes, while summer means rafting tours and kayaking on the Youghiogheny River right outside of town.
Deep Creek Lake, a destination for bass fishermen, beckons adventure seekers with boating, water skiing, and more, while Deep Creek Lake State Park is home to some of the area's most satisfying hiking and camping.
When the lake freezes over, try your hand at ice fishing. Never gone dog sledding? You'll get your chance at Husky Power in the nearby town of Accident, where sled dogs pull passengers over snow and dry ground alike.
No matter the season, our vacation rentals in Oakland, MD are your key to the beauty of the Deep Creek area!
The 10 Best Hiking Trails Near Deep Creek Lake
The Best Deep Creek Lake Cabins for Any Season
Photo Credit: marabuchi via Flickr
