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Search results; Over 1,000 homes in Oakland

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Top guest favourite
Holiday home in Oakland
Lakefront Cabin in Stunning Storybook Setting
3 bedrooms, 6 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.97 out of 5 average rating, 145 reviews
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Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
12–17 Oct
4.88 out of 5 average rating, 112 reviews
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Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 192 reviews
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Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 170 reviews
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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
27 Sept – 2 Oct
4.92 out of 5 average rating, 26 reviews
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Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 122 reviews
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Superhost
Home in Oakland
Lakefront 4BR with a great view!
4 bedrooms, 6 beds
20–25 Sept
New place to stay
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Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
4–9 Oct
4.88 out of 5 average rating, 32 reviews
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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
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Guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds
30 Nov – 5 Dec
4.89 out of 5 average rating, 55 reviews
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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
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Guest favourite
Home in Oakland
Brand NEW, Lake Access, Dog Friendly, Hot Tub
3 bedrooms, 3 king beds
9–14 Nov
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed
20–25 Sept
4.98 out of 5 average rating, 206 reviews
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Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
4–9 Oct
4.91 out of 5 average rating, 54 reviews
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Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds
30 Sept – 5 Oct
4.99 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Oakland
The Barn @ Silo Farm | Deep Creek Lake, MD
2 bedrooms, 4 beds
24–29 Sept
5.0 out of 5 average rating, 60 reviews
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Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 34 reviews
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Guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds
2–7 Nov
4.9 out of 5 average rating, 60 reviews