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Search results; Over 1,000 homes in Oakland

Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds, 2 private bathrooms
9–14 Aug
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4.9 out of 5 average rating, 264 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Cabin in Oakland
7BR Luxury Log Home, pool, hottub, near Deep Creek
7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Jul
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 41 reviews
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.88 out of 5 average rating, 52 reviews
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
4 bedrooms, 8 beds, 4 bathrooms
9–14 Aug
New place to stay
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.71 out of 5 average rating, 14 reviews
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
1 bedroom, 1 double bed, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 81 reviews
Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
2 bedrooms, 3 beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 168 reviews
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.73 out of 5 average rating, 86 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
19–24 Jul
4.9 out of 5 average rating, 49 reviews
Superhost
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.85 out of 5 average rating, 81 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
24–29 Jul
5.0 out of 5 average rating, 171 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 158 reviews