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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 private bathrooms
2–7 Nov
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4.9 out of 5 average rating, 59 reviews
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
13–18 Sept
5.0 out of 5 average rating, 186 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
13–18 Sept
4.85 out of 5 average rating, 26 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
28 Sept – 3 Oct
4.88 out of 5 average rating, 111 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
7–12 Sept
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 34 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 88 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds
11–16 Sept
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 167 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 395 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
7–12 Sept
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds
7–12 Sept
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 120 reviews
Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 reviews
Guest favourite
Home in Oakland
Serene Mountain Escape: Hot Tub, Foosball, Views!
5 bedrooms, 8 beds
13–18 Sept
4.94 out of 5 average rating, 93 reviews
Top guest favourite
Chalet in Oakland
The Dacha - Cozy with Lake Views, Hot Tub,
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 163 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
14–19 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds
26–31 Oct
5.0 out of 5 average rating, 83 reviews