
Holiday houses in Oakland
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Molly
Molly has a garage style window that opens up overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles from 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 - check other things to note about pets.

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.

The cozy cottage!
Hidden away in a serene natural atmosphere you will find our cozy cottage. This is an up to date, stylish and cozy cottage in North Glade on Oakway Rd. Perfect weekend retreat for a couple or a solo peaceful stay. The cottage has an open floor plan with all modern finishes. New furniture and modern appliances for your convenience. Stylish kitchen with open shelving, flat top stove with built in air fryer, farm sink, large under the counter fridge, microwave and keurig. No shared spaces.

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.

1BR Romantic Couples Getaway!
Looking for a relaxing getaway with your significant other? We have you covered! Deep Creek Charm is nestled in the woods just a few minutes from Deep Creek Lake and all it has to offer! Enjoy the summer nights with the newly added outdoor firepit or soaking in the hot tub. For the colder evenings you can sit in by the cozy indoor fireplace and read a good book or watch tv on the large flat screen. You'll leave relaxed and ready to come back again in the future. Hope to see you soon!

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.

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

The Davis Loft - The Best Location in Davis!
The Davis Loft is the closest home rental to Blackwater Falls and is within walking distance to all that Davis has to offer. The loft has all the modern touches you would expect but still retains the right amount of rustic nostalgia that blends in so perfectly with the culture and landscape of the magnificent Canaan Valley. Have a front row seat to one of the most beautiful places in eastern North America.
Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland

The Country Nook at Waters Run Farmlands w/WI-FI

Alpine Lake Resort Cabin - Hot Tub Pool Golf Beach

Josie

Victorian Farmhouse with view of pleasant valley

Alice’s Place

Relaxing Romantic Cabin*HotTub*Pets*Walk To Lake

C Box MountainTop

Peaceful nature retreat nestled in a forested area
Quick stats about holiday rentals in Oakland
Total holiday rentals
Explore 10 holiday rentals in Oakland
Nightly prices starting at
Oakland holiday rentals start at $105 NZD per night before taxes and fees
Verified guest reviews
Over 750 verified reviews to help you choose
Pet-friendly accommodation
Find 10 rentals that welcome pets
Wi-Fi availability
10 of Oakland holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Oakland rentals
4.8 Average rating
Oakland stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- New York City Holiday rentals
- Western North Carolina Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- Niagara Falls Holiday rentals
- Fallingwater
- Timberline Mountain
- Seven Springs Mountain Resort
- Wisp Resort
- Ohiopyle State Park
- Blackwater Falls State Park
- Canaan Valley Resort & Conference Center
- Pete Dye Golf Club
- Lakeview Golf Resort
- White Grass
- Canaan Valley Ski Resort
- Pikewood National Golf Club
- Lodestone Golf Course
- Winter Experiences at The Peak
- Warden Lake
- Forks of Cheat Winery
- Mountain Dragon Mazery Fine Honey Wine
- West Whitehill Winery