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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bathroom
14–19 Sept
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4.97 out of 5 average rating, 231 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.86 out of 5 average rating, 28 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, 169 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, 189 reviews
Guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
4–9 Oct
4.95 out of 5 average rating, 57 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
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds
13–18 Sept
4.91 out of 5 average rating, 56 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds
7–12 Dec
5.0 out of 5 average rating, 117 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
14–19 Sept
4.92 out of 5 average rating, 25 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
Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 reviews
Top guest favourite
Home in Oakland
Broadford Park View
5 bedrooms, 8 beds
20–25 Sept
4.95 out of 5 average rating, 41 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds
12–17 Sept
4.99 out of 5 average rating, 67 reviews
Guest favourite
Chalet in Oakland
Private (5 Star!) Lake Access Chalet w/ Hot Tub
3 bedrooms, 5 beds
13–18 Sept
4.95 out of 5 average rating, 373 reviews
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds
17–22 Sept
4.89 out of 5 average rating, 19 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
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds
13–18 Sept
4.84 out of 5 average rating, 459 reviews