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Search results; Over 1,000 homes in Oakland

Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 bed, 1 shared bathroom
9–14 Aug
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4.98 out of 5 average rating, 203 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 177 reviews
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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.82 out of 5 average rating, 22 reviews
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.87 out of 5 average rating, 15 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.89 out of 5 average rating, 107 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 208 reviews
Guest favourite
Home in Accident
Peaceful nature retreat nestled in a forested area
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 140 reviews
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.73 out of 5 average rating, 89 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds, 1 bathroom
15–20 Nov
4.99 out of 5 average rating, 214 reviews
Top guest favourite
Farm stay in Terra Alta
Pachamama’s Garden
1 bedroom, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Home in Oakland
The Barn @ Silo Farm | Deep Creek Lake, MD
2 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 56 reviews
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.9 out of 5 average rating, 269 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 180 reviews
Guest favourite
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 38 reviews