Oakland Vacation Rentals

Compare 43 vacation rentals.
USA > Maryland > Oakland

Make Oakland your next getaway

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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Popular amenities for Oakland vacation rentals

Popular
Dog-friendly Hot tub Internet
Lakeview Loft
1 Bedroom | 1 Bath | Sleeps 4

Lakeview Loft - Oakland, MD

$116 avg / night
The Lake House
5 Bedroom | 5 Bath | Sleeps 14

The Lake House - Oakland, MD

$432 avg / night
A Million Dollar View
3 Bedroom | 3.5 Bath | Sleeps 5

A Million Dollar View - Oakland, MD

$403 avg / night
High Mountain Villa
3 Bedroom | 2 Bath | Sleeps 8

High Mountain Villa - Oakland, MD

$135 avg / night
Recreational Therapy
2 Bedroom | 1 Bath | Sleeps 5

Recreational Therapy - Oakland, MD

$149 avg / night

View 38 more homes

Recent Oakland guest reviews

Beautiful countryside, very relaxing...just what I went for!
Cindy I. | May 2024
I loved this house it was absolutely amazing. My friends and I had a blast as it was our last trip together!! I would recommend this to anyone and I would 100% come back
ivy f. | May 2024
This place is good for the money. Its just a 5 minute walk to Swallow Falls. We enjoyed our stay. It's not a fancy place by no means but it actually exceeded my expectations for the low cost.
Robert D. | May 2024
Oakland vacation rental FAQ

Yes, 40 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. 111 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