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Oakland Vacation Rentals

25 Oakland Vacation Rentals were found matching your criteria.


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Red Run Cabin

  4 reviews   Add to Favorites

Cabin: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States


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Cozy Cabin

Cabin: 3 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States


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Herrington House

Cottage: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States


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All Seasons

  4 reviews   Add to Favorites

Home: 4 Bedroom, 2.5 Bathroom, Sleeps 9
Location: Oakland, Maryland, United States


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Glamping-Cortina

  1 reviews   Add to Favorites

Home: 1 Bedroom, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States


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$345 - $481 /night
$1479 - $2131 /week
Adorable Pet Friendly Family Home with Hot Tub

  75 reviews   Add to Favorites

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States


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$1397 - $2066 /night
$5890 - $9387 /week
Beautiful Lakefront Home w/ Private Indoor Pool, Hot Tub ...

  41 reviews   Add to Favorites

Home: 8 Bedroom, 7.5 Bathroom, Sleeps 26
Location: Oakland, Maryland, United States


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Lazy Bear Lodge

  4 reviews   Add to Favorites

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 13
Location: Oakland, Maryland, United States


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Whispering Heights

  4 reviews   Add to Favorites

Home: 5 Bedroom, 3 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States


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Bear Crossing

  66 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 10
Location: Oakland, Maryland, United States


$537 - $913 /night
$2278 - $4991 /week
Exceptional 5 Bedroom on Premiere level lakefront!

  8 reviews   Add to Favorites

Home: 5 Bedroom, 4.5 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States


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Windy Acres

  2 reviews   Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States


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Swallow Hollow

  66 reviews   Add to Favorites

Home: 2 Bedroom, 2 Bathroom, Sleeps 10
Location: Oakland, Maryland, United States


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Glamping-Stanley

Home: 1 Bedroom, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States


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Shenandoah

  37 reviews   Add to Favorites

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 14
Location: Oakland, Maryland, United States


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Blarney Stone Manor

  53 reviews   Add to Favorites

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Oakland, Maryland, United States


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Wild Yough Villa

  49 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States


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Mystic Creek Villa

  2 reviews   Add to Favorites

Home: 5 Bedroom, 4.5 Bathroom, Sleeps 13
Location: Oakland, Maryland, United States


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Finches' Nest

Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States


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Glamping-Ardennen

Home: 1 Bedroom, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States


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Glamping-Uzes

  1 reviews   Add to Favorites

Home: 1 Bedroom, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States


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Deck on the Lake

  5 reviews   Add to Favorites

Home: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States


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Relaxation Station

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States


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Tall Pines

  25 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Oakland, Maryland, United States


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Dolce Vita

Home: 4 Bedroom, 3 Bathroom, Sleeps 10
Location: Oakland, Maryland, United States


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