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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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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, 194 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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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
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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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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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 28 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
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
18–23 Oct
4.95 out of 5 average rating, 58 reviews
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Flat in Oakland
Charming 1-bdrm with balcony, Close to Everything.
1 bedroom, 1 single bed, 1 bathroom
2–7 Oct
4.7 out of 5 average rating, 27 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, 399 reviews
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Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 207 reviews
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Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
26–31 Oct
4.88 out of 5 average rating, 32 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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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
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 183 reviews
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Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 20 reviews
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Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
25–30 Oct
4.92 out of 5 average rating, 98 reviews