Vacation rentals in Oakland

The Original Hob

We have the Original Hob and Molly (separate listing) overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared sweet kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles of State Parks and Deep Creek Lake. Come see the Garrett County stars, hear the creek and birds and be a million miles from where you are. Friendly dogs are welcomed -see "other things to note".

Mountain Air Oasis with Hot Tub

Relax with the whole family or friends at this peaceful private 2 acre property, close to Maryland's natural attractions! A family-friendly three bedroom home 1,380 sq. ft secluded in a rural neighborhood. Wildlife to watch and enjoy! Relax with a campfire or soak in the hot tub! We are located approximately 30 minutes from Swallow Falls State Park, Deep Creek Lake, and Black Water Falls State Park. We are also within 10 minutes of two wedding venues (The White Barn, and Twin Tales Event Farm).

Ella Bella Chalet: Hot Tub, Stunning Views, Wi-Fi

Welcome to Ella Bella Chalet! Escape to our modern, yet cozy cabin boasting panoramic breathtaking views and an array of upscale amenities. Relax in the hot tub under starlit skies or gather around the fire pit for cozy evenings. Located near Wisp Ski Resort, golf courses, and endless lake activities, including boating, fishing, tubing and kayaking. Explore nearby hiking trails and attractions like Swallow Falls State Park, Adventure Sports Center International, zip lining, biking, and more.

Dancing Bears

***PLEASE NO PETS*** Meticulously maintained authentic log cabin in the woods getaway! Our 800 sf cabin has two bedrooms, one bathroom and large bonus 3rd bedroom/loft area (queen bed, two cots, kids' play area, TV and home office space). Our location is secluded yet conveniently located to all of the activities Deep Creek Lake has to offer. The property backs up to 65 wooded acres at the end of a private road. Peaceful setting with a stream, fire pit, picnic table, and horse shoe pit.

The View

Spacious, clean, modern basement efficiency apartment. Private entrance, private bath w/shower, private kitchenette with full size fridge & microwave (no stove), 1 queen size bed. Pool table, bar area and living room space with large TV equipped with satellite service. More space than a hotel room. View of Deep Creek Lake from front lawn in the distance, 11 Miles to Wisp, 6 miles to Deep Creek State Park and 1 mile to Thousand Acres Golf Course. NO Smoking, No Pets. We now have WIFI!!

SUGARBUSH - Sweet Serenity Tiny House

Welcome to SUGARBUSH! "Suga" is a 450 sq. ft. custom built tiny house. She will comfortably accommodate 2 adults or a family with 2 small children. AGE REQUIREMENT to book this space is 25+. At this time we DO NOT allow pets. Suga sits on a 3+ acre lot that use to be used for cross country skiing. She got her name from two trails, Sugarbush Run and Sugarbush Shortcut that ran through the lot! We welcome you to stay and enjoy our wonderful little getaway here in Pleasant Valley.

Lake View Loft Lodge on Deep Creek Lake

Seconds away from the lake, Trader's Coffee House, Brenda's Pizzeria, High Mountain Sports, and minutes away from Wisp Ski Resort, entertainment, shopping, food, and anything else you could want. Just eight miles south of Deep Creek Lake is historic Oakland, MD. Oakland is known for its small-town feel with local restaurants, small businesses, and popular festivals. Taking the time to visit Downtown Oakland is a must-see on your to-do list at Deep Creek Lake.

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

Pet friendly-Cottage in the Woods

Tucked conveniently between Swallow Falls State Park and Deep Creek Lake, this recently renovated 2 bd cottage has everything you need for a weekend getaway or a much needed week(s) long vacation!  Inside you will find a completely stocked kitchen, open living/dining area,  full size bathroom, 2 bedrooms and a cozy nook with sleeper sofa and desk.  Relax and unwind in the spacious backyard or charming balcony. *pets stay free