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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
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4.96 out of 5 average rating, 215 reviews
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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.86 out of 5 average rating, 29 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 169 reviews
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
Guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
4–9 Oct
4.95 out of 5 average rating, 57 reviews
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
Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 121 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 88 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
12–17 Sept
4.91 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds
20–25 Sept
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
14–19 Sept
4.98 out of 5 average rating, 50 reviews
Guest favourite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds
13–18 Sept
4.93 out of 5 average rating, 68 reviews
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
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Holiday home in Oakland
Lakefront Cabin in Stunning Storybook Setting
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Townhouse in McHenry
Our Lovely Lake Retreat
3 bedrooms, 4 beds
11–16 Oct
5.0 out of 5 average rating, 110 reviews
Top guest favourite
Home in Oakland
Summer Fun at our Lake View Condo!
3 bedrooms, 4 beds
12–17 Sept
4.97 out of 5 average rating, 128 reviews