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Search results; Over 1,000 homes in Oakland

Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 private bathrooms
12–17 Jul
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4.98 out of 5 average rating, 158 reviews
Guest favourite
Home in Oakland
The Other House
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
4.97 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 205 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Cabin in Oakland
7BR Luxury Log Home, pool, hottub, near Deep Creek
5.0 out of 5 average rating, 17 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, 103 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 171 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul
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
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.95 out of 5 average rating, 41 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Cabin in Terra Alta
Peaceful Cabin w/ Private Dock & Kayaks
4.95 out of 5 average rating, 40 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 41 reviews, 1 bed, 1 bathroom
13–18 Jul
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
C Box MountainTop
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 88 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
4.98 out of 5 average rating, 63 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
12–17 Jul
Guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
4.94 out of 5 average rating, 168 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept