
Vacation rentals in Oakland
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Top-rated vacation 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.

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).

Luxurious Couples Getaway; Private Pond! Hot Tub!
Private Pond nestled in the pines just a mile from Deep Creek Lake State Park, Hot Tub, Outdoor TV, Cozy Rocking Chairs, Propane Fire Pit, Soaking Tub, Robes, Plush King Bed with Pond Views, Espresso Machine, Margaretaville Margarita Machine, Sound Appealing? Then this is the cabin for you! Just a couple hundred yards from Deep Creek Lake and only 1 mile from the state park! Our cabin is tucked in the pines and is specifically tailored for a quiet, romantic getaway with your significant other!

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.

Lakefront Cabin in Stunning Storybook Setting
Reconnect with nature, relax, recharge, & rejuvenate. Our newly updated cabin & incredible setting is just what you need. Lakefront views with boat slip, kayak, hot tub & more. Come enjoy this one of a kind home for fishing (a trout brook runs through our property), bird watching, meteor showers, boating, foliage, horseback riding or skiing (10 mins from Wisp). Within mins you’ll find: hiking, ATV riding, white water raffling, countless farms & restaurants & more. IG page at CampLittleBearMD.

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.

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 birdhouse
Off grid. All solar. Private 15 acres. 3 miles from Wisp ski resort 3 miles from Beautiful deep Creek Lake. Spectacular view a birdwatchers paradise. 3 miles from Youghiogheny river A rafters kayakers boaters paradise. A true Vista. short drives to spectacular hiking biking trails. Top class river rafting in Friendsville Youghiogheny River four and five class Rapids. Many other activities nearby and also many restaurants. You can also arrange activities with host. Just make a wish list.

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.

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.

Captain's Quarters Deep Creek Log Cabin Oasis
Welcome to our slice of peace and relaxation in beautiful Deep Creek! Spacious and serene log cabin. The Captains Quarters is the perfect getaway. 2BDRM, propane fireplace (Nov-Apr), full kitchen, and a 6+ person hot tub. Dogs welcome but please let us know and pay the fee. 2 comfy Queen mattresses, towels and linens provided, hi speed internet, smart TV’s, and Bluetooth soundbar. Relax in our two heated massage chairs in the family room. We want to earn a 5 star review!
Popular amenities for Oakland vacation rentals
Other great vacation rentals in Oakland

The Little Fox Den *Lake View*

LakeShore LoftHouse

One bedroom Loft-15 from WISP & close to Walmart

Broadford Park View

Sleeps 10 • Lakeview • FirePit/Hottub • 8 min lake

"Das Haus Am See" (the house at the lake)

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

The Tiny House @ Deep Creek Lake
Quick stats about vacation rentals in Oakland

Total vacation rentals
Explore 10 vacation rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at $83 CAD per night before taxes and fees

Verified guest reviews
Over 860 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Oakland vacation rentals include wifi 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!
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- Wisp Resort
- Fallingwater
- Timberline Mountain
- Seven Springs Mountain Resort
- Ohiopyle State Park
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- White Grass
- Canaan Valley Ski Resort
- Blackwater Falls State Park
- Tygart Lake
- Laurel Hill State Park
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- West Virginia University
- Deep Creek Lake State Park
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- Hidden Valley Resort
- Fort Necessity National Battlefield
- Lodestone Golf Course
- Smoke Hole Caverns
- Audra State Park
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