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Search results; Over 1,000 homes in Oakland

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Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bathroom
17–22 Sept
,
4.97 out of 5 average rating, 231 reviews
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Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 192 reviews
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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
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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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Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
4.98 out of 5 average rating, 170 reviews
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Top guest favourite
Home in Oakland
The Barn @ Silo Farm | Deep Creek Lake, MD
2 bedrooms, 4 beds, 1.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 60 reviews
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Guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 182 reviews
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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
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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
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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
4–9 Oct
4.91 out of 5 average rating, 54 reviews
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Top guest favourite
Holiday home in Oakland
Lakefront Cabin in Stunning Storybook Setting
3 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 145 reviews
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Guest favourite
Home in Oakland
Kestrel's Keeps
4 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 87 reviews
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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
11–16 Oct
4.98 out of 5 average rating, 50 reviews
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Guest favourite
Home in Oakland
Serene Mountain Escape: Hot Tub, Foosball, Views!
5 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
4.94 out of 5 average rating, 94 reviews
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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
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Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 34 reviews
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Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 67 reviews
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Guest favourite
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
4.83 out of 5 average rating, 168 reviews
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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 26 reviews