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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
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5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
28 Sept – 3 Oct
4.89 out of 5 average rating, 110 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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
6–11 Sept
4.85 out of 5 average rating, 26 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, 167 reviews
Superhost
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds
7–12 Sept
4.88 out of 5 average rating, 251 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
14–19 Sept
4.92 out of 5 average rating, 24 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, 185 reviews
Top guest favourite
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds
26–31 Oct
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
7–12 Sept
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Home in Oakland
Broadford Park View
5 bedrooms, 8 beds
9–14 Sept
4.95 out of 5 average rating, 41 reviews
Cabin in Oakland
Rustic Swallow Falls Cabin 2
1 bedroom, 2 beds
2–7 Sept
New place to stay
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, 394 reviews
Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
7–12 Sept
4.98 out of 5 average rating, 49 reviews
Guest favourite
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds
3–8 Sept
4.83 out of 5 average rating, 167 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
13–18 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Cabin in Oakland
Swallow Falls Cabin 4
3 bedrooms, 3 double beds
2–7 Sept
New place to stay