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Search results; Over 1,000 homes in Oakland

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Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 3 beds, 1 private bathroom
11–16 Sept
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4.96 out of 5 average rating, 211 reviews
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Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 110 reviews
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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
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Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.85 out of 5 average rating, 26 reviews
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Superhost
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds, 5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 166 reviews
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Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
7–12 Sept
4.9 out of 5 average rating, 52 reviews
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Guest favourite
Cabin in Oakland
Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub
7 bedrooms, 12 beds, 4 bathrooms
20–25 Sept
4.91 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds, 2 bathrooms
3–8 Sept
4.92 out of 5 average rating, 13 reviews
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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, 87 reviews
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Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 85 reviews
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Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
13–18 Sept
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Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 49 reviews
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Home in Oakland
Vintage Oakland @ Oakland, Maryland
4 bedrooms, 8 beds, 3 bathrooms
8–13 Sept
4.26 out of 5 average rating, 23 reviews
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Superhost
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 53 reviews
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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, 274 reviews
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Guest favourite
Cabin in McHenry
Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTD
6 bedrooms, 9 beds, 4 bathrooms
7–12 Sept
4.96 out of 5 average rating, 166 reviews
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Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 119 reviews