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Search results; Over 1,000 homes in Oakland

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
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.75 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
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 102 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
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
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds, 2 bathrooms
9–14 Jul
4.88 out of 5 average rating, 52 reviews
Guest favourite
Home in McHenry
Deep Creek Gem: Hot Tub, Spa Bath & Game Room
4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Home in Oakland
Spring is in the air at our Lake View Condo!
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 122 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.94 out of 5 average rating, 51 reviews
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
4.85 out of 5 average rating, 447 reviews
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
2 bedrooms, 2 queen beds, 2 bathrooms
28 Jul – 2 Aug
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Jul
4.98 out of 5 average rating, 82 reviews
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
19–24 Jul
4.92 out of 5 average rating, 85 reviews
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.73 out of 5 average rating, 88 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