Oakland Vacation Rentals

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USA > Maryland > Oakland

Make Oakland your next getaway—choose from 37 great vacation rentals

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. 

Explore Oakland house rentals, cabins, condo rentals, and more

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House rentals

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Cabins

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Condo rentals

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Oakland vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Recreational Therapy
2 Bedroom | 1 Bath | Sleeps 5

Recreational Therapy - Oakland, MD

$132 avg / night
Luxury Lake
4 Bedroom | 5.5 Bath | Sleeps 12

Luxury Lake - Oakland, MD

$595 avg / night
Lakeview Loft
1 Bedroom | 1 Bath | Sleeps 4

Lakeview Loft - Oakland, MD

$112 avg / night
Swallow Falls Cabin #1
1 Bedroom | 1 Bath | Sleeps 4

Swallow Falls Cabin #1 - Oakland, MD

$108 avg / night
Incognito
3 Bedroom | 2 Bath | Sleeps 8

Incognito - Oakland, MD

$147 avg / night

View 32 more homes

Recent Oakland vacation rental reviews

We enjoyed our stay at this well-appointed home. It had all we needed for a long weekend skiing at Wisp. The kids loved the bunk room and having their own TV. We were nervous about the steep grade getting to the house with the snow, but our AWD SUV did fine. It was quite chilly the first night and most of the thermostats were locked, but once the house heated up, it was comfortable.
Theresa L. | Jan 2023
Booked this house for my birthday get away. The house was great, clean, and accommodating to all parties. The wifi was sometimes spotty and water wasn’t always warm. The photos aren’t up to date, the TVs are actually way more up to date and kitchen is as well. I would definitely book again minus the small hiccups.
William H. | Jan 2023
Wonderful house, plenty of space.
Ann K. | Jan 2023
Oakland vacation rental FAQ

Yes, 17 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. 54 of our Oakland vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Oakland vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

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 >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Oakland, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Oakland, MD: A Main Street Community

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.

Year-Round Outdoor Adventure in Oakland, MD

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!

Discover Oakland

The 10 Best Hiking Trails Near Deep Creek Lake

The Best Deep Creek Lake Cabins for Any Season

 Photo Credit: marabuchi via Flickr