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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.88 out of 5 average rating, 111 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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.85 out of 5 average rating, 26 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 185 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 167 reviews
Superhost
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 251 reviews
Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds, 2 bathrooms
4–9 Sept
4.83 out of 5 average rating, 167 reviews
Cabin in Oakland
Swallow Falls Cabin 3
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
New place to stay
Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 14 reviews
Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 reviews
Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 206 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 394 reviews
Home in Oakland
Camp David at The Yough
4 bedrooms, 6 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Home in Oakland
Broadford Park View
5 bedrooms, 8 beds, 3.5 bathrooms
10–15 Sept
4.95 out of 5 average rating, 41 reviews
Guest favourite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds, 1.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 67 reviews