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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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4.89 out of 5 average rating, 110 reviews
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
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
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 88 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 205 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
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
Cottage on Jericho Road
4.75 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
4.9 out of 5 average rating, 243 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Oakland
The Wise Quack - A Taste of Deep Creek Lake!
4.82 out of 5 average rating, 132 reviews, 3 bedrooms, 5 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Cabin in Oakland
C Box MountainTop
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
4.9 out of 5 average rating, 264 reviews, 2 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Home in Oakland
New 5 Bedroom Home, Lake View, King Beds
4.74 out of 5 average rating, 46 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
10–15 Jul
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 158 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.95 out of 5 average rating, 41 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
5.0 out of 5 average rating, 6 reviews, 6 bedrooms, 7 beds, 2.5 bathrooms
21–26 Jul
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
4.93 out of 5 average rating, 81 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul