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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Spacious Home Near All Deep Creek MD Has to Offer
4 bedrooms, 6 beds, 3 private bathrooms
24–29 Jul
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4.9 out of 5 average rating, 108 reviews
Top guest favourite
Home in Oakland
The Other House
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
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
13–18 Sept
Superhost
Home in Oakland
Pet Friendly Cabin - Private & Quiet Neighborhood
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
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
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
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 169 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Superhost
Home in Oakland
Prime Location w Hot tub & Firepit
New place to stay, 5 bedrooms, 7 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
4.96 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 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
5–10 Jul
Top guest favourite
Cabin in Oakland
Luxury 7BR Cabin|HotTub|HeatedPool
5.0 out of 5 average rating, 17 reviews, 7 bedrooms, 10 beds, 4 bathrooms
7–12 Oct
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
5.0 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Cabin in Oakland
C Box MountainTop
4.94 out of 5 average rating, 50 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Home in Oakland
Cottage on Jericho Road
4.71 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
4.95 out of 5 average rating, 385 reviews, 2 bedrooms, 2 beds, 2 bathrooms
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
5–10 Jul
Superhost
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
4.85 out of 5 average rating, 81 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
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