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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
Lakehound Lodge - lake view, pet friendly
3 bedrooms, 3 beds, 3 private bathrooms
7–12 Sept
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4.92 out of 5 average rating, 267 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
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, 1 bathroom
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, 4 bathrooms
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, 2 bathrooms
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, 1 bathroom
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, 2.5 bathrooms
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, 2 bathrooms
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, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 115 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 bathroom
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, 3.5 bathrooms
27 Aug – 1 Sept
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.94 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 38 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 393 reviews
Top guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.96 out of 5 average rating, 307 reviews