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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 Oct
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4.96 out of 5 average rating, 216 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
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
17–22 Sept
4.98 out of 5 average rating, 170 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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Top guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
4–9 Oct
4.87 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
18–23 Oct
4.95 out of 5 average rating, 57 reviews
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Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 16 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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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
20–25 Sept
4.92 out of 5 average rating, 26 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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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
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds
11–16 Oct
4.92 out of 5 average rating, 97 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
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews
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Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds
18–23 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds
17–22 Sept
4.93 out of 5 average rating, 68 reviews
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Guest favourite
Townhouse in Oakland
LakeView Nook - Walk to Coffee Shop & Boat Slip
1 bedroom, 2 beds
27 Sept – 2 Oct
4.9 out of 5 average rating, 20 reviews
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Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds
12–17 Oct
4.91 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 87 reviews
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Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 34 reviews