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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 3 beds, 1 private bathroom
11–16 Oct
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4.96 out of 5 average rating, 215 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 30 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
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
18–23 Oct
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.91 out of 5 average rating, 54 reviews
Guest favourite
Home in McHenry
Cozy Lake House with Dock
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
4.92 out of 5 average rating, 119 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 88 reviews
Guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.89 out of 5 average rating, 54 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
28 Sept – 3 Oct
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Oakland
Broadford Park View
5 bedrooms, 8 beds, 3.5 bathrooms
21–26 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds, 5 bathrooms
17–22 Oct
4.91 out of 5 average rating, 56 reviews
Guest favourite
Cabin in Oakland
Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room
7 bedrooms, 12 beds, 4 bathrooms
20–25 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 114 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
2–7 Oct
4.92 out of 5 average rating, 97 reviews