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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.98 out of 5 average rating, 179 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
4.97 out of 5 average rating, 110 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Oakland
Cottage on Jericho Road
4.75 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Top guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
5.0 out of 5 average rating, 18 reviews, 7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 104 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 207 reviews, 2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
Guest favourite
Home in Oakland
The Other House
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Home in Oakland
New! Lake Area Home w/ Hot Tub
New place to stay, 4 bedrooms, 4 beds, 3 bathrooms
17–22 Jul
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.95 out of 5 average rating, 44 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.89 out of 5 average rating, 104 reviews, 5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 172 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 159 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 42 reviews, 1 bed, 1 bathroom
18–23 Aug
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
4.85 out of 5 average rating, 447 reviews, 3 bedrooms, 6 beds, 1 bathroom
1–6 Aug
Top guest favourite
Cabin in Oakland
The Falls Cabin ↟↟ secluded log cabin in the woods
4.98 out of 5 average rating, 116 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Jul
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
4.98 out of 5 average rating, 64 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
17–22 Jul
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
4.86 out of 5 average rating, 83 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
4.92 out of 5 average rating, 85 reviews, 3 bedrooms, 5 beds, 3 bathrooms
9–14 Aug