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.

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).

The Falls Cabin ↟↟ secluded log cabin in the woods

hello, and welcome to @thefallscabin! we are so happy you’re here. :) the falls cabin sits quietly tucked away on 11 wooded acres, located just minutes from deep creek lake, swallow falls state park, and wisp resort. it is the perfect spot for getting away from the noise – but being close to it all. the cabin is equipped with brand-new furniture, mattresses, etc. follow us @thefallscabin for more photos and progress as we continue to flip this lovely place into our modern, wooded oasis.

Treehouse in Deep Creek Lake

Newly built, Whispering Woods is a custom-made treehouse surrounded by stunning scenery just minutes from Deep Creek Lake and Wisp Resort. No detail was overlooked in the spacious interior that includes 2 bedrooms, 2 baths, a fully equipped kitchen, and a sitting area with a 65” TV. The amazing outdoor living space includes expansive decks, a fire pit, and a bubbling hot tub. For a unique and memorable experience from start to finish, come relax and reconnect at this treetop escape.

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.

Spring Sale! Hot Tub & Fire Pit! Roomy House!

🎉 Discounts - Save 8–10%! Book 6+ months ahead, stay 1+ weeks! ✅Within walking distance to the lake! ✅Pool Table, darts, multipurpose game table, board games, cards. ✅Plenty of parking ✅Lake access from the neighborhood dock are extra perks!*cozy beds ✅large deck ✅Hot Tub ✅huge dining table ✅make s'mores at the firepit ✅walk around the quiet neighborhood ✅Relax/watch the wildlife walk through yard. ✅TVs in every room provide entertainment for all!

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*

Peaceful nature retreat nestled in a forested area

Welcome to our lovely vacation House! Built in 2024, fresh, cozy and modern. Perfect for memorable family trip, romantic getaway for a couple or a fun adventure for a small group of friends. Convenient location- great combination of privacy (forest-like area) and quick access to fun places: 5-10 minutes drive from Wisp Ski Resort, Deep Creek lake, boat rentals, scenic hikes, restaurants, bars, amusement parks and grocery stores.

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

That Special Place (lake view, hot tub 4 bedroom)

Relax with the whole family at this peaceful place to stay. 4 bedroom cabin in excellent location with a wonderful view of the lake. Enjoy NBA jam and Blitz video consoles. 3 Queen beds 2 queen bunk beds Hot tub Firepit Gas fireplace Pets welcome 75 additional. Please use retaining pond area or cabin lawn to walk dog. Do not use lot at the end of Glendale woods road. 4 wheel drive in the winter is recommended

Private (5 Star!) Lake Access Chalet w/ Hot Tub

Escape to tranquility at this secluded chalet nestled in the woods, just a short walk to Deep Creek Lake. Indulge in the ultimate relaxation with a private hot tub, offering stunning views of the surrounding nature. Perfect for couples, small families, or solo adventurers seeking a peaceful getaway. Close to tons of hiking & biking trails, Swallow falls state park, Wisp ski resort, and much more!

Bev's House at Sunny Meadows

Looking for a place to stay that is quiet and relaxing, but also close to many outdoor activities? Bev's House at Sunny Meadows is just that! Located just minutes from several state parks that offer boating, fishing, kayaking, swimming, hiking and biking, there's always plenty to do. Bev's House offers a quiet place with spectacular mountain views to escape the rush and noise of everyday life.