Search For Vacation Homes in Oakland

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Featured Vacation Homes in Oakland

Bear Hollow Lodge

Bear Hollow Lodge

4 out of 5
20590 GARRETT HWY Oakland MD
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Stay at this vacation home in Oakland. Enjoy a pool table, balconies, and cable TV channels. Popular attractions Deep Creek Lake and Wisp Resort are located ...
Bears Lair

Bears Lair

4 out of 5
94 LEHMAN LN Oakland MD
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Stay at this vacation home in Oakland. Enjoy free parking, patios, and cable TV channels. Popular attractions Deep Creek Lake and Wisp Resort are located ...
Acorn Cottage

Acorn Cottage

4.5 out of 5
3164 Lake Shore Drive Oakland MD
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Book a stay at this luxury vacation home in Oakland. Enjoy a marina, private hot tubs, and furnished balconies or patios. Popular attractions Deep Creek Lake ...
Loft of Luxury

Loft of Luxury

4 out of 5
Oakland MD
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Stay at this vacation home in Oakland. Enjoy free parking, cable TV channels, and in-room fireplaces. Popular attractions Deep Creek Lake and Wisp Resort are ...
Picture Perfect

Picture Perfect

3.5 out of 5
1195 MOUNTAINVIEW DR Oakland MD
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Stay at this vacation home in Oakland. Enjoy free parking, a pool table, and balconies or patios. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
Butterfly Retreat

Butterfly Retreat

4 out of 5
1489 MOUNTAINVIEW DR Oakland MD
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Stay at this vacation home in Oakland. Enjoy free parking, patios, and cable TV channels. Popular attractions Deep Creek Lake and Wisp Resort are located ...
Laurel Brook 39

Laurel Brook 39

3.5 out of 5
Oakland MD
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Stay at this vacation home in Oakland. Enjoy a pool table and in-room fireplaces. Popular attractions Deep Creek Lake and Wisp Resort are located nearby.
Bee Tree II

Bee Tree II

4 out of 5
1379 Lakeshore Drive Oakland MD
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Stay at this 4-star vacation home in Oakland. Enjoy free parking, balconies or patios, and cable TV channels. Popular attractions Deep Creek Lake and Deep Creek ...
Kare Bear Cabin

Kare Bear Cabin

3.5 out of 5
158 GLENDALE RD Oakland MD
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Stay at this vacation home in Oakland. Enjoy free parking, cable TV channels, and in-room fireplaces. Popular attractions Deep Creek Lake and Wisp Resort are ...
Mountain Freedom

Mountain Freedom

4 out of 5
705 MOUNTAINVIEW DR Oakland MD
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Stay at this vacation home in Oakland. Enjoy a pool table, balconies or patios, and in-room fireplaces. Popular attractions Deep Creek Lake and Wisp Resort are ...
A Beautiful View

A Beautiful View

4 out of 5
41 FOX DEN RD Oakland MD
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Stay at this vacation home in Oakland. Enjoy in-room fireplaces and a restaurant. Popular attractions Deep Creek Lake and Wisp Resort are located nearby.
Chateau Relaxo

Chateau Relaxo

3.5 out of 5
589 MOUNTAINVIEW DR Oakland MD
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Stay at this vacation home in Oakland. Enjoy free parking, patios, and cable TV channels. Popular attractions Deep Creek Lake and Wisp Resort are located ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Can't find what you're looking for? Check out these other accommodation options...

The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
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Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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