Oakland Rentals

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27 Houses

Red Run Cabin

Oakland log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful, clean home in a perfect setting!” My husband, two year old daughter, dog and I just returned from a five night stay at Red Run Cabin. The home, although nothing fancy, was beautiful and well kept. We generally always stay in cabins or condos when we travel and this was by far the cleanest rental we've stayed in. It is located in a quiet, wooded neighborhood, with the lake right across the street with easy "beach" access. Our ten year old nephew who lives in the area and came to visit loved the game room with bumper pool and fooseball. We also made use of the plentiful board games available and watched several of the multitude of older movies to choose from when it was raining. Our family loved grilling out with us (charcoal and propane provided) and roasting smores over the firepit. My husband and I spent every night relaxing in the hot tub after our toddler and dog had settled in for the night. The home does not have air conditioning (which I believe is common for the area) but plenty of fans that allowed us to stay fairly comfortable in the Springtime mid 70's weather. The kitchen was equipped very well, although it may be time to invest in some new knives. John, the owner, was a very kind and patient and you can tell he takes great pride in his rentals. Whenever we come this way again, we will definitely return to Red Run Cabin.

Price per night from

$245

Great rentals within 20 miles that match your search

White Oak Retreat

Swanton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

“Lovely place for family vacation!” This spacious log house was a perfect fit for our first family trip to Deep Creek. We had plenty of room for our group of 11 people (3 couples and 5 single adults). Everyone was pleased with the accommodations. It was clean, spacious and well equipped. John & Kathy Joyce were a pleasure to deal with. They were very helpful from beginning to end. We had such a good time that we hope to visit again next year.

Price per night from

$401

Rock Haul

Swanton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

“Relaxing at the lake!!” Peaceful and quiet. Plenty of room for family. Right on the lake. Kitchen has everything needed to cook. Cozy and clean with rustic charm!!

Price per night from

$372

Deep Creek Log Home Sleeps 10

McHenry house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$287

Price per night from

$490

Yorkie Acres Farm Yurt & Farm Experience

Friendsville yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$103

Serene 3BR Lake House w/ breathtaking views

Terra Alta house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$320

CABIN PRIVATE ALPINE LAKE WITH HIKING AND GOLF COURSE GATED COMMUNITY

Terra Alta house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$161

Mountain Escape Deep Creek Lake Maryland

McHenry house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$973

Calling all mountain bike enthusiasts! Welcome to Cavie House!!

Davis house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$165

Beautiful custom built home offers peace and quiet in a beautiful setting.

Canaan Valley house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$200

Clean, convenient and comfortable and all in the same place!

Canaan Valley house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$175

Convenient location meets affordable pricing at Pendletonheim 1B.

Davis apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$130

Cottage on Chipmunk Alley in Davis

Davis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$103

Private Lake/Beach Cabin, Golf, Fire Pit, & WiFi!

Terra Alta log cabin

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 34 minutes

Price per night from

$64

NEW!! The Cabin located in Alphine Lake Resort

Terra Alta log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$185

Porch Paradise

Terra Alta house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

Responds fast! avg. 29 minutes

Price per night from

$308

Rustic and Charming Cozy Cabin

Terra Alta log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$172

Cozy escape, enjoy this lake-view home!

Terra Alta house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 29 minutes

Price per night from

$330

Bearadise Cabin

Terra Alta log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 29 minutes

Price per night from

$385

Private Lake/Beach Cabin w/Golf, Pool, Fire pit

Terra Alta house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 34 minutes

Price per night from

$63

Beautiful home within walking distance to lake!

Terra Alta house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 29 minutes

Price per night from

$264

Deer Ridge-watch the deer while relaxing in nature

Terra Alta log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$197

New! Wintervue with Fireplace - Pet Friendly Home

Terra Alta chalet

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 29 minutes

Price per night from

$420

New!! Mcferson located in Alphine Lake Resort

Terra Alta house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$372

NEW!! Lake Escape located in Alphine Lake Resort

Terra Alta house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 29 minutes

Price per night from

$401

Amazing cabin with porch and whirlpool tub!

Terra Alta log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 29 minutes

Price per night from

$211

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About Oakland

Located in the beautiful mountains of western Maryland, Oakland is the perfect woodland escape. Be the first to see the sun hit the green hills from your vacation home's bedroom balcony, then walk just minutes to Deep Creek Lake, perfect for boating, tubing, hiking, and swimming. Feel free to bring the water skis and kayak as there is plenty of space inside your vacation rental to store your equipment. While you are here, spend a day at Swallow Falls State Park, home to some of Maryland's most beautiful natural scenery. Hike along trails with panoramic views of rocky gorges, flowing rapids, and Muddy Creek Falls, a thrashing 53-foot waterfall. The park offers a large picnic area with a pavilion and playground, as well as nature programs, boat rentals, and a beach for swimming during the summer.

Here are a few additional suggestions of things to do in the area:

  • Visit Maryland's Historic B&O Train Station: This authentic 1884 train station has been restored to its original Queen Anne condition. The train speaks to Oakland's old, small town feel and adjoins a shop that sells baked goods, candles and maple syrup.
  • See a show at Our Town Theatre: This little production company offers great local and imported talent. Be sure to check the current schedule while visiting, and catch great comedies, dramas, and more.
  • Visit the county's Historical Society Museum: Like the train station, the historical museum is a great place to learn about the area's history and get a feel for small town life in another era.
  • Play golf: Champion caliber Deep Creek golf courses offer some of the best greens in the state. After a day of golf, spend an afternoon indulging in a pedicure at a luxury Deep Creek spa.
  • Go horseback riding: Several private stables in the state park area offer one-on-one lessons or trail rides with a friendly knowledgeable guide.
  • Experience Deep Creek skiing: In the winter, Deep Creek offers pristine, powdery trails perfect for both cross country and downhill skiing.

Experience the best of Oakland and the Deep Creek Lake area by staying in your own private luxury vacation rental. A trendy winter condo or summer apartment rental may be perfect for a long weekend getaway with friends. You may also decide to host your family and friends for a barbeque at your lakeside vacation home or mountain cabin. While you're visiting Oakland, make the most of your stay by scheduling a visit to nearby Swanton or McHenry.

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