Oakland Vacation Rentals

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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, condo rentals, cabins, and more

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House rentals

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Condo rentals

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Cabins

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Oakland vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Great Escape
2 Bed | 2 Bath | Sleeps 10

Great Escape - Oakland, MD

$437 avg / night
(excludes fees and taxes)
4.0 (75)
High Mountain Villa
3 Bed | 2 Bath | Sleeps 8

High Mountain Villa - Oakland, MD

$185 avg / night
(excludes fees and taxes)
4.35 (43)
Oakland Oasis
2 Bed | 2 Bath | Sleeps 4

Oakland Oasis - Oakland, MD

$207 avg / night
(excludes fees and taxes)
5.0 (2)
Woodsy Way Cabin
2 Bed | 2 Bath | Sleeps 9

Woodsy Way Cabin - Oakland, MD

$232 avg / night
(excludes fees and taxes)
4.54 (39)
Owl's Landing
2 Bed | 1 Bath | Sleeps 6

Owl's Landing - Oakland, MD

$139 avg / night
(excludes fees and taxes)
3.79 (43)

View 26 more homes

Recent Oakland vacation rental reviews

The house is very nice and pleasing to stay in. The house and properties around it were clean and well maintained. Plenty of parking. The location was fantastic. Just a few minutes from the lake and less than a minute drive to stores and restaurants. The only downsides were the mattresses were old and very worn. They need replaced. The Wi-Fi was at times slow. But, was not always terrible. We would definitely stay here again.
STEVEN R. | Jul 2025
We loved this house so much! It was clean and well stocked with anything you could want in a house.
Jacquelyn H. | Jul 2025
We loved the layout of this cabin. It has a huge kitchen for gathering and the bedrooms are spaced out to give privacy with single floor living. Finishes were nice and we felt like cool kids camping out in a new A frame with huge windows giving views of the surrounding forest. The location in the deep creek area is also perfect. We loved being close to Swallow falls and Harrington with backdoor access to anywhere on Deep Creek lake. We did try to walk down to the Yough river, but were thwarted by a wall of mountain laurel. You could maybe pull this off in a different season. The reason for 4 stars was the comfort of the bedrooms. There is zero bedroom furniture forcing you to live off the ground out of your suitcase. The closets are massive, but unless you plan on hanging all your clothes, aren't terribly useful. The bunkbed room was nice, but the other two bed heights were very awkward. The king was basically on the ground and the other room with the queen was awkwardly high to the point where I at 5'10" almost had to jump in. And no night stands. Another negative was that the grill was unusably dirty, and not just the grates. The trap area was so full that it lit on fire as soon as we turned it on creating a dangerous situation. That puts a damper on summer cookouts. Also the fridge ice maker doesn't work . If they get the bedroom furniture and grill sorted out this place is a slam dunk.
Michael A. | Jul 2025
Oakland Frequently Asked Questions

Yes, 13 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. 82 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

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