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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
Wooded camp w/lake views/fire pit. Great location.
3 bedrooms, 4 beds, 2 private bathrooms
5–10 Aug
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4.86 out of 5 average rating, 159 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 10 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, 107 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.8 out of 5 average rating, 20 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
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
9–14 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, 113 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.96 out of 5 average rating, 48 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, 162 reviews
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 37 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 84 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 44 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, 390 reviews
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
4.89 out of 5 average rating, 247 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds, 1 bathroom
12–17 Oct
4.99 out of 5 average rating, 211 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 179 reviews
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
4 bedrooms, 8 beds, 4 bathrooms
10–15 Aug
New place to stay