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Search results; Over 1,000 homes in Oakland

Guest favourite
Cottage in Oakland
Deep Creek Lake Cozy Cottage (Dog Friendly)
3 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.98 out of 5 average rating, 107 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 181 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.83 out of 5 average rating, 23 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
17–22 Aug
4.89 out of 5 average rating, 108 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
25–30 Aug
4.96 out of 5 average rating, 208 reviews
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Accident
Peaceful nature retreat nestled in a forested area
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 143 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds, 1 bathroom
15–20 Nov
4.99 out of 5 average rating, 214 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
4.98 out of 5 average rating, 164 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 310 reviews
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.89 out of 5 average rating, 248 reviews
Top guest favourite
Cabin in Oakland
Molly
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.99 out of 5 average rating, 168 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 55 reviews
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 271 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Farm stay in Terra Alta
Pachamama’s Garden
1 bedroom, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 71 reviews