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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Sunlit Lakefront w/ Dock, Game Room & Firepit
4 bedrooms, 8 beds, 4.5 shared bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oakland
The Other House
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.89 out of 5 average rating, 104 reviews, 5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 102 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Cabin in Oakland
7BR Luxury Log Home, pool, hottub, near Deep Creek
5.0 out of 5 average rating, 17 reviews, 7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 41 reviews, 1 bed, 1 bathroom
12–17 Jul
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
Home in Oakland
Cottage on Jericho Road
4.75 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 171 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul
Top guest favourite
Cabin in Oakland
C Box MountainTop
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
New place to stay, 4 bedrooms, 8 beds, 4 bathrooms
9–14 Aug
Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Jul
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 86 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
4.98 out of 5 average rating, 92 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Superhost
Home in Oakland
Pet-Friendly, Hot Tub, Beautiful Mountain Cabin
4.89 out of 5 average rating, 9 reviews, 3 bedrooms, 7 beds, 1 bathroom
8–13 Jul
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.95 out of 5 average rating, 40 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4.9 out of 5 average rating, 49 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
19–24 Jul
Guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
5.0 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
4.93 out of 5 average rating, 80 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul