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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
,
4.98 out of 5 average rating, 179 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 102 reviews
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.71 out of 5 average rating, 14 reviews
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
1 bedroom, 1 double bed, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.94 out of 5 average rating, 50 reviews
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 168 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
4.92 out of 5 average rating, 85 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
4.96 out of 5 average rating, 203 reviews
Top guest favourite
Cabin in Terra Alta
Peaceful Cabin w/ Private Dock & Kayaks
4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 40 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 158 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Oakland
Spring is in the air at our Lake View Condo!
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.97 out of 5 average rating, 122 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 385 reviews
Guest favourite
Home in Oakland
The Wise Quack - A Taste of Deep Creek Lake!
3 bedrooms, 5 beds, 2 bathrooms
28 Jul – 2 Aug
4.82 out of 5 average rating, 131 reviews