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Holiday Lettings
> North America
> United States
> Maryland
> Garrett County
> Houses and Chalets in Oakland

Houses in Oakland and Chalets – Holiday Lettings - Holiday Rentals Oakland

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£1 £750 -

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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133 Holiday homes

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Oakland holiday log cabin rental

Oakland log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Quiet relaxation” Set in a quiet cove, this cabin provides it all. For the kids, hot tub, wifi, cable TV and games, along with lake access. For the parents, a quiet, relaxing retreat away from, but with easy access to, the main roads. The addition of the State Park pass makes visiting nearby Swallow Falls and Herrington Manor even more inviting. Getting to events, activities, restaurants, shopping and museums in Oakland and McHenry is a breeze. Staying here means being able to take advantage of all Deep Creek has to offer without the hassle of being right in the middle of everything. It also means vacationers can, if they choose, lay in supplies, never leave the property and enjoy being away from it all. For those wanting to get away, this is the place to do it.

30 reviews

from £208 / night

£875 - £1,934 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £226 / night

£1,576 / week

1 / 29

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from £166 / night

£1,160 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £100 / night

£698 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

from £322 / night

£2,252 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £181 / night

£1,267 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £262 / night

£1,830 / week

1 / 24

Ski home to rent in Oakland

Oakland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £80 / night

£558 / week

1 / 28

Holiday home in Oakland

Oakland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £125 / night

£873 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £149 / night

£1,042 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

from £277 / night

£1,937 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £226 / night

£1,582 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £236 / night

£1,650 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £165 / night

£1,154 / week

1 / 30

Holiday home in Oakland

Oakland house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

from £462 / night

£3,231 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £63 / night

£439 / week

1 / 22

Ski home to rent in Oakland

Oakland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £283 / night

£1,982 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £409 / night

£2,860 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £146 / night

£1,019 / week

1 / 29

Holiday home rental

Oakland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £148 / night

£1,030 / week

1 / 25

Holiday home in Oakland

Oakland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

from £205 / night

£1,430 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £161 / night

£1,126 / week

1 / 14

Oakland ski home to rent.

Oakland house

  • 10 bedrooms
  • 14 bathrooms
  • sleeps 34

from £816 / night

£5,708 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £101 / night

£704 / week

1 / 30

Oakland ski chalet to rent.

Oakland chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

from £266 / night

£1,858 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

from £355 / night

£2,483 / week

1 / 30

Holiday home in Oakland

Oakland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £99 / night

£693 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £181 / night

£1,267 / week

1 / 25

Holiday home in Oakland

Oakland house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £361 / night

£2,528 / week

1 / 30

Home rental in Oakland

Oakland house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £334 / night

£2,336 / week

1 / 16

Ski home to rent in Oakland

Oakland house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £144 / night

£1,008 / week

1 / 30

Holiday home in Oakland

Oakland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £78 / night

£541 / week

1 / 30

Ski home to rent in Oakland

Oakland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £96 / night

£670 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £102 / night

£710 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £356 / night

£2,488 / week

1 / 30

Oakland holiday home let

Oakland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from £134 / night

£935 / week

1 / 28

Ski home to rent in Oakland

Oakland house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 8

from £115 / night

£800 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

from £272 / night

£1,903 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £366 / night

£2,561 / week

1 / 30

Oakland ski home to rent.

Oakland house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from £131 / night

£918 / week

1 / 30

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Oakland holidays

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 holiday 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 holiday 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 programmes, 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 cheque 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 calibre 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 holiday 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 holiday 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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