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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bathroom
26–31 Jul
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4.96 out of 5 average rating, 227 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 Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
4.97 out of 5 average rating, 33 reviews
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, 88 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, 103 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
4.96 out of 5 average rating, 205 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
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
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 243 reviews
Guest favourite
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
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.94 out of 5 average rating, 51 reviews
Guest favourite
Home in Oakland
The Wise Quack - A Taste of Deep Creek Lake!
3 bedrooms, 5 beds, 2 bathrooms
28 Aug – 2 Sept
4.82 out of 5 average rating, 132 reviews
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.9 out of 5 average rating, 264 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, 42 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.95 out of 5 average rating, 42 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
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
4.88 out of 5 average rating, 52 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
24–29 Aug
4.95 out of 5 average rating, 386 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.93 out of 5 average rating, 81 reviews