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Search results; Over 1,000 homes in Oakland

Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 bed, 1 shared bathroom
27 Jul – 1 Aug
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4.98 out of 5 average rating, 201 reviews
Guest favourite
Home in Oakland
The Other House
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
4.98 out of 5 average rating, 64 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
5.0 out of 5 average rating, 18 reviews, 7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
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
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 104 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 172 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 207 reviews, 2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Superhost
Home in Swanton
Lakefront w Private Dock, Hot Tub, Large Yard
New place to stay, 5 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.95 out of 5 average rating, 44 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 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
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 160 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Home in Oakland
New! Lake Area Home w/ Hot Tub
New place to stay, 4 bedrooms, 4 beds, 3 bathrooms
28 Jul – 2 Aug
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
5.0 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
4.94 out of 5 average rating, 170 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
4.97 out of 5 average rating, 110 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 42 reviews, 1 bed, 1 bathroom
18–23 Aug
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
4.98 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul