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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds
9–14 Aug
4.96 out of 5 average rating, 208 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
23–28 Aug
4.82 out of 5 average rating, 22 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 11 beds
20–25 Sept
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
9–14 Aug
4.89 out of 5 average rating, 108 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
15–20 Aug
5.0 out of 5 average rating, 177 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 163 reviews
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 115 reviews
Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds
9–14 Aug
4.97 out of 5 average rating, 230 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
27 Aug – 1 Sept
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds
16–21 Aug
4.92 out of 5 average rating, 38 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds
20–25 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds
19–24 Sept
4.96 out of 5 average rating, 307 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
16–21 Aug
4.95 out of 5 average rating, 393 reviews
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed
9–14 Aug
4.73 out of 5 average rating, 89 reviews
Guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds
9–14 Aug
4.89 out of 5 average rating, 9 reviews
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds
10–15 Aug
4.83 out of 5 average rating, 166 reviews