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Search results; Over 1,000 homes in Oakland

Guest favourite
Chalet in Oakland
Private (5 Star!) Lake Access Chalet w/ Hot Tub
3 bedrooms, 5 beds, 2 private bathrooms
22–27 Aug
,
4.95 out of 5 average rating, 368 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
15–20 Aug
5.0 out of 5 average rating, 177 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 10 beds
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
9–14 Aug
4.89 out of 5 average rating, 107 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds
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
30 Aug – 4 Sept
4.97 out of 5 average rating, 114 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
10–15 Aug
4.82 out of 5 average rating, 22 reviews
Home in Oakland
Lainee Jayne's at Deep Creek Lake
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 162 reviews
Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds
9–14 Aug
4.97 out of 5 average rating, 230 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
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
4 bedrooms, 8 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
2 bedrooms, 4 beds
16–21 Aug
4.98 out of 5 average rating, 94 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds
30 Aug – 4 Sept
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
16–21 Aug
4.95 out of 5 average rating, 392 reviews
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Chalet in Oakland
Log chalet w/ hot tub & BBQ grill
5 bedrooms, 8 beds
23–28 Aug
4.83 out of 5 average rating, 54 reviews
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds
10–15 Aug
4.83 out of 5 average rating, 166 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds
16–21 Aug
4.98 out of 5 average rating, 65 reviews