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Search results; Over 1,000 homes in Oakland

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
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 17 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
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
4.88 out of 5 average rating, 52 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
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
2 bedrooms, 2 queen beds, 2 bathrooms
28 Jul – 2 Aug
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.97 out of 5 average rating, 109 reviews
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.75 out of 5 average rating, 16 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
Superhost
Home in Oakland
Pet-Friendly, Hot Tub, Beautiful Mountain Cabin
3 bedrooms, 7 beds, 1 bathroom
8–13 Jul
4.89 out of 5 average rating, 9 reviews
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.72 out of 5 average rating, 87 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
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
2 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.98 out of 5 average rating, 92 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
4.94 out of 5 average rating, 51 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
Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
2 bedrooms, 3 beds, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds, 3 bathrooms
19–24 Jul
5.0 out of 5 average rating, 104 reviews