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Search results; Over 1,000 homes in Oakland

Top guest favourite
Chalet in Oakland
Happy Our Retreat. Amazing Lake/Mtn Views!
3 bedrooms, 4 beds, 2 private bathrooms
31 Aug – 5 Sept
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4.96 out of 5 average rating, 172 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds
13–18 Sept
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
5–10 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed
12–17 Jul
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Oakland
7BR Luxury Log Home, pool, hottub, near Deep Creek
7 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
27 Jul – 1 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds
6–11 Jul
4.94 out of 5 average rating, 50 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
19–24 Jul
5.0 out of 5 average rating, 169 reviews
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
2 bedrooms, 2 queen beds
6–11 Jul
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
19–24 Jul
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
12–17 Jul
4.98 out of 5 average rating, 158 reviews
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
18–23 Jul
4.71 out of 5 average rating, 14 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
12–17 Jul
4.95 out of 5 average rating, 385 reviews
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
2 bedrooms, 4 beds
5–10 Jul
4.98 out of 5 average rating, 92 reviews
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed
5–10 Jul
4.73 out of 5 average rating, 86 reviews
Superhost
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
3 bedrooms, 4 beds
12–17 Jul
4.85 out of 5 average rating, 81 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds
28 Jul – 2 Aug
4.96 out of 5 average rating, 203 reviews
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds
2–7 Aug
4.94 out of 5 average rating, 168 reviews