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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 bed, 1 private bathroom
6–11 Aug
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4.98 out of 5 average rating, 179 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 175 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Home in Oakland
The Other House
4.95 out of 5 average rating, 19 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
5.0 out of 5 average rating, 82 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Home in Oakland
Cottage on Jericho Road
4.78 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 89 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.9 out of 5 average rating, 105 reviews, 5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 208 reviews, 2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 161 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Barn in Oakland
Couples Retreat: The HayLoft- Rustic Escape For 2
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Cabin in Oakland
C Box MountainTop
4.94 out of 5 average rating, 53 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
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
22–27 Jul
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
4.97 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Farm stay in Terra Alta
Pachamama’s Garden
5.0 out of 5 average rating, 67 reviews, 1 bedroom, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
4.99 out of 5 average rating, 85 reviews, 2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
Guest favourite
Hut in Oakland
Large estate, miles of trails, cozy hut Cortina
4.91 out of 5 average rating, 102 reviews, 1 bedroom, 2 beds, 6 bathrooms
26–31 Jul
Flat in Oakland
Charming 1-bdrm with balcony, Close to Everything.
4.72 out of 5 average rating, 25 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 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
6–11 Aug
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.96 out of 5 average rating, 45 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug