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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
29 Jul – 3 Aug
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4.96 out of 5 average rating, 228 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
18–23 Jul
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds
25–30 Oct
5.0 out of 5 average rating, 104 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
19–24 Jul
4.94 out of 5 average rating, 17 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds
19–24 Jul
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 160 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds
9–14 Aug
4.96 out of 5 average rating, 207 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
23–28 Aug
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
26–31 Jul
5.0 out of 5 average rating, 172 reviews
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
1 bedroom, 1 double bed
19–24 Jul
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 110 reviews
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed
2–7 Aug
4.73 out of 5 average rating, 89 reviews
Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed
6–11 Aug
4.98 out of 5 average rating, 179 reviews
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds
21–26 Sept
4.94 out of 5 average rating, 170 reviews
Top guest favourite
Barn in Oakland
Couples Retreat: The HayLoft- Rustic Escape For 2
1 bedroom, 1 king bed
20–25 Jul
5.0 out of 5 average rating, 18 reviews