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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
,
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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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, 394 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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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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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
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 82 reviews
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Guest favourite
Cabin in Oakland
Pool, HotTub, FirePit, EVCharger, & Great Location
6 bedrooms, 10 beds, 4.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 126 reviews
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Top guest favourite
Home in Swanton
Almost Heaven
4 bedrooms, 7 beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 33 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, 54 reviews
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Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 94 reviews