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.

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Top guest favorite

Treehouse in McHenry

5 out of 5 average rating, 117 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 favorite

Tiny home in Oakland

4.97 out of 5 average rating, 188 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 favorite

Home in Oakland

4.97 out of 5 average rating, 115 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 favorite

Vacation home in Oakland

4.97 out of 5 average rating, 106 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 favorite

Cabin in Oakland

4.96 out of 5 average rating, 215 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.

Superhost

Home in Oakland

4.85 out of 5 average rating, 141 reviews

Beautiful LAKE VIEW w/HOT TUB, Fire Pit & GameRoom

You will love this breathtaking views around the house and overlooking the lake towards WISP Ski resort! Come make the best memories with friends and family while enjoying everything Deep Creek Lake has to offer. We offers a peaceful more secluded area that is only minutes from Wisp Ski Resort, restaurants, Bars, Golfing, Mini Golf, High ropes course, Mountain coaster, White water rafting. Spacious parking, large deck with a slide, new kitchen, coffee bar, game room and so much more!

Top guest favorite

Cabin in Oakland

4.98 out of 5 average rating, 171 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.

Top guest favorite

Cabin in Deep Creek

4.98 out of 5 average rating, 126 reviews

Boulder Ridge Cabin, close to Deep Creek, Maryland

Boulder Ridge Cabin is surrounded by woods, but within 15 minutes of Deep Creek Lake, swimming, boating, hiking, shopping, restaurants, Wisp Resort with skiing, snowboarding, mountain coaster, whitewater rafting at Adventure Sports Center International, rock climbing, hiking. Swallow Falls State Park and Herrington Manor State Park are about 15 minutes drive. Piney Mountain State Forest is within walking distance. Mountain biking and fishing are also close by.

Top guest favorite

Home in Oakland

4.94 out of 5 average rating, 117 reviews

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.

Top guest favorite

Cottage in Oakland

4.95 out of 5 average rating, 140 reviews

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*

Guest favorite

Cottage in Oakland

4.92 out of 5 average rating, 179 reviews

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

Guest favorite

Chalet in Oakland

4.97 out of 5 average rating, 313 reviews

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!