Oakland Vacation Rentals

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Make Oakland your next getaway—choose from 32 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


House rentals

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View 7 Cabins

Condo rentals

View 6 Condo rentals

Oakland vacation rentals for every getaway

Dog-friendly Hot tub Internet
Tees 'N Skis 3D Tour
4 Bed | 3.5 Bath | Sleeps 10

Tees 'N Skis - Oakland, MD

From $124
Z Lake Retreat 3D Tour
3 Bed | 2.5 Bath | Sleeps 8

Z Lake Retreat - Oakland, MD

From $89
Still Meadows 3D Tour
3 Bed | 1 Bath | Sleeps 6

Still Meadows - Oakland, MD

From $140
Great Escape 3D Tour
2 Bed | 2 Bath | Sleeps 10

Great Escape - Oakland, MD

From $200
Bee Tree II 3D Tour
4 Bed | 3 Bath | Sleeps 10

Bee Tree II - Oakland, MD

From $325

View 27 more homes

Recent Oakland vacation rental reviews

We had a lovely time. House is comfortable and basement functioned as a "granny flat" in reverse. Young adults and 1 pet in the basement and geriatrics stayed upstairs with other pet. Nearby trails was great for youth.
Diana G. | Sep 2021
First off the cabin is as nice as it looks in the pictures which isn't always the case when we go away. But we never knew about the deep creek area and most certainly will be coming back. So much to see and do in the area all within 10 minutes.
Eric C. | Sep 2021
The cabin was very clean upon arrival. Check in and check out extremely easy and hassle-free. The location and size of the cabin were perfect for the two of us to celebrate our ten year wedding anniversary. Would definitely return.
Jolene D. | Sep 2021

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