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

$139 avg / night
Luxury Lake
4 Bedroom | 5.5 Bath | Sleeps 12

Luxury Lake - Oakland, MD

$547 avg / night
Lakeview Loft
1 Bedroom | 1 Bath | Sleeps 4

Lakeview Loft - Oakland, MD

$133 avg / night
Swallow Falls Cabin #1
1 Bedroom | 1 Bath | Sleeps 4

Swallow Falls Cabin #1 - Oakland, MD

$112 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 loved everything about this house! It was clean, spacious & well furnished. The location was perfect, it is 10 minutes from Wisp resort which was a plus! The manager (Richard) of this property was very kind, patient and helpful. Since this was my first time renting from Vacasa I had a lot of questions and he was available to answer all of them. It was very helpful that he was local and knew the area well.
Keith G. | Nov 2022
Had a wonderful time spending the holiday at Still Meadows. The made it special b adding Thanksgiving plates napkins and even two roasting pans. The home was spotless and there was an abundance of towels. We highly recommend this place for a back to nature experience
Deborah B. | Nov 2022
Thanks for the peaceful thanksgiving weekend
Dale H. | Nov 2022
Oakland Frequently Asked Questions

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. 53 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