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Search results; Over 1,000 homes in Oakland

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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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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 27 reviews
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Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 192 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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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
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 124 reviews
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Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 171 reviews
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Superhost
Castle in Oakland
Mountaintop Castle @ Deep Creek Lake w/ Alpacas
7 bedrooms, 27 beds, 5.5 bathrooms
1–6 Oct
4.75 out of 5 average rating, 8 reviews
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Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 48 reviews
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Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.88 out of 5 average rating, 32 reviews
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Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.74 out of 5 average rating, 91 reviews
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Guest favourite
Cabin in Oakland
Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room
7 bedrooms, 12 beds, 4 bathrooms
7–12 Oct
4.92 out of 5 average rating, 25 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
25–30 Oct
4.95 out of 5 average rating, 398 reviews
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Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed, 1 bathroom
1–8 Oct
4.63 out of 5 average rating, 70 reviews
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Guest favourite
Home in Oakland
Brand NEW, Lake Access, Dog Friendly, Hot Tub
3 bedrooms, 3 king beds, 3.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 5 reviews
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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
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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
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Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 10 reviews