Holiday houses in Oakland

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

Fern Hill Cabin - rustic cabin near Deep Creek

Enjoy a comfortable rustic cabin with two bedrooms, one full bathroom, a powder room, spacious living room, kitchen and a dining area. Outside you can relax on a large screened porch or by the firepit under a blanket or stars. Some of the most beautiful areas such as Swallow Falls, Herrington Manor and Rock Maze are only a short drive away. Enjoy skiing at Wisp Resort or boating and swimming at Deep Creek State Park. Many wonderful restaurants and fun things to do are also a short drive away.

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).

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.

Tree House

Wintertime readiness: When we have snow, 4-wheel or All-wheel drive will be best. Watch the weather. Un plug at Tree House. There is no Wi-Fi. We provide a TV w/ DVDs. There’s a cabin smart phone for your use if you do not have phone service. A 15 minute drive takes you to Thomas, WV for food and art and music (and Wi-Fi).Five more minutes and you are in Davis for Blackwater Falls State Park. A few more miles down the road find two alpine ski areas and White Grass Ski Touring Center.

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.

The Wise Quack - A Taste of Deep Creek Lake!

Welcome to The Wise Quack - our cozy cottage in the center of Deep Creek Lake activities…all 4 seasons! Ski at Wisp Resort, kayak on the Youghiogheny River, hike, bike, golf, horseback ride, boat or lay on a sandy beach. Surrounded by 8 state parks. Family-friendly, the WQ, has all the comforts of home with a full kitchen, WIFI, DISH TV, grill, fire pit, tiny house game room and deck to view the wildlife surrounding you. Early check-in & late check-out=more time to enjoy!

New! The Butterfly Suite at Enchanted Table Meadow

Minutes from Wisp Ski Resort & Deep Creek Lake! Come as you are & take a seat at nature’s table under the canopy of stars. Embrace the wooded ambiance and meadow views from our 825 sq. ft suite as you melt your cares away in front of the fireplace. Located between I-68 and Deep Creek Lake/Wisp. Our hope is to provide a serene landscape where you can find peace and rest through nature. Our setup works well for business travelers & as a couple's romantic escape!

Dandy Flats - The Nonchalant

Located in a historic building on the main drag and adorned with 135-year old hardwood floors, original woodwork, local art, huge rain shower, and forest views - this tastefully styled flat feels like being transported to a 19th century boarding house. With espresso, galleries, live music, shops, food, and drinks steps away, you have the forests and a tiny cityscape just steps out your door. This apartment is offered at the Dandy Flats - a lovingly restored Inn.

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.

The Nest near Deep Creek

Kick back and relax in this calm, stylish space. Brand new, beautiful one bedroom apartment above a detached garage just 5 miles from Deep Creek Lake. Beautifully designed space with craftsman quality large kitchen, king size neo-industrial walnut bed, live-edge vanity and wall cap, articulating lamp, all made by local craftsman. Leather pull out couch with queen bed sleeps two extra guests. Relax by the fire pit and listen to the birds in the woods.