Vacation rentals in Oakland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
Treehouse in McHenry
4.99 out of 5 average rating, 192 reviews

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.

Top guest favourite
A cozy sleeping area features wooden walls and a warmly patterned bedspread. Light streams in through two windows, illuminating the space. A bedside lamp and a wicker storage unit add functional elements, while a comfortable chair provides additional seating.
Tiny homes in Oakland
4.97 out of 5 average rating, 197 reviews

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".

Top guest favourite
A spacious outdoor hot tub is positioned on a patio, featuring soft blue lighting and a clear water surface. It is surrounded by green grass and trees in the background.
Home in Oakland
4.98 out of 5 average rating, 152 reviews

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).

Top guest favourite
A cozy cabin is nestled among lush greenery, featuring a welcoming porch with comfortable seating. A stone pathway leads through landscaped areas with shrubs and rocks, enhancing the natural surroundings. Soft lighting from the cabin adds a warm ambiance to the outdoor space.
Cabin in Swanton
4.99 out of 5 average rating, 108 reviews

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!

Guest favourite
The exterior showcases a charming chalet surrounded by trees, featuring a spacious wrap-around deck with patio seating and a fire pit area. The large windows reflect the warm indoor lights, revealing an inviting atmosphere that complements the natural surroundings.
Chalet in Swanton
4.94 out of 5 average rating, 157 reviews

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.

Top guest favourite
The exterior of a wooden cabin is framed by tall trees, with warm light glowing from the large front windows. A spacious deck is visible at the entrance, surrounded by lush greenery and natural stone pathways leading through the forest.
Vacation home in Oakland
4.97 out of 5 average rating, 136 reviews

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.

Top guest favourite
The entrance to the cabin is framed by natural wood logs, featuring double black doors that open onto a spacious porch. A welcome mat sits at the base of the door, while snow gently falls onto the wooden deck surrounded by trees.
Cabin in Oakland
4.98 out of 5 average rating, 110 reviews

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.

Top guest favourite
The cabin exterior features a handcrafted log design with a peaked roof. A welcoming porch encircles the front, supported by sturdy wooden posts. Surrounded by lush greenery, the structure blends harmoniously with the natural setting of the wooded area.
Cabin in Oakland
4.96 out of 5 average rating, 225 reviews

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.

Top guest favourite
A serene sleeping area features a spacious bed with soft pillows and a textured blanket. Natural wood elements are present in the design, complemented by vivid wall art depicting foliage. Large windows allow for ample natural light and offer views of the surrounding greenery.
Treehouse in Friendsville
4.94 out of 5 average rating, 227 reviews

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.

Top guest favourite
The tiny house features a wooden exterior, complemented by a sloped metal roof. A wooden deck with two chairs is positioned at the entrance, surrounded by greenery. Large windows allow natural light to fill the living space, offering a connection with the outdoors.
Cabin in Oakland
4.98 out of 5 average rating, 177 reviews

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.

Guest favourite
Treehouse in McHenry
4.96 out of 5 average rating, 135 reviews

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.

Top guest favourite
The log cabin exterior features a spacious wooden deck, furnished with several chairs and a dining table. Lush green grass surrounds the cabin, and a fire pit area is visible to the side. Trees provide a natural backdrop, enhancing the serene environment.
Cabin in Oakland
4.97 out of 5 average rating, 103 reviews

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

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!

  1. Airbnb
  2. United States
  3. Maryland
  4. Garrett County
  5. Oakland