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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
Mountain Escape - Hot Tub, Game Room, Fire Pit
3 bedrooms, 5 beds, 2.5 private bathrooms
23–28 Aug
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4.85 out of 5 average rating, 198 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
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, 181 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
17–22 Aug
4.89 out of 5 average rating, 108 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
4.98 out of 5 average rating, 164 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
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
25–30 Aug
4.96 out of 5 average rating, 208 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, 116 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, 5 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 46 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
16–21 Aug
4.97 out of 5 average rating, 230 reviews
Home in Oakland
Cozy Dog Friendly Wooded Home w/ Hot Tub
5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
New place to stay
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 65 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 Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 34 reviews
Superhost
Home in Oakland
Lakefront Luxury -Theater Dock Hot Tub - Sleeps 16
7 bedrooms, 8 beds, 6 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 180 reviews
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds, 1 bathroom
19–24 Aug
4.85 out of 5 average rating, 452 reviews