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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
2–7 Oct
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4.86 out of 5 average rating, 161 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
13–18 Sept
5.0 out of 5 average rating, 188 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
8–13 Sept
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
8–13 Sept
4.91 out of 5 average rating, 54 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
28 Sept – 3 Oct
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 34 reviews
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds
9–14 Sept
5.0 out of 5 average rating, 113 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.85 out of 5 average rating, 27 reviews
Top guest favourite
Holiday home in Oakland
Lakefront Cabin in Stunning Storybook Setting
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 145 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 88 reviews
Superhost
Castle in Oakland
Mountaintop Castle @ Deep Creek Lake w/ Alpacas
7 bedrooms, 27 beds
8–13 Sept
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds
14–19 Sept
4.97 out of 5 average rating, 231 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds
11–16 Sept
4.99 out of 5 average rating, 67 reviews
Guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
4–9 Oct
4.94 out of 5 average rating, 54 reviews
Guest favourite
Home in Oakland
Serene Mountain Escape: Hot Tub, Foosball, Views!
5 bedrooms, 8 beds
13–18 Sept
4.94 out of 5 average rating, 94 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews