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Search results; Over 1,000 homes in Oakland

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
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
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 169 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
Superhost
Home in Oakland
Prime Location w Hot tub & Firepit
5 bedrooms, 7 beds, 3 bathrooms
19–24 Jul
New place to stay
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
Cabin in Oakland
Luxury 7BR Cabin|HotTub|HeatedPool
7 bedrooms, 10 beds, 4 bathrooms
7–12 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 179 reviews
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
4.73 out of 5 average rating, 86 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
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
Guest favourite
Home in Oakland
Value Stay*Lots of Privacy w Hot Tub-Firepit-Games
5 bedrooms, 13 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 5 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 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
Superhost
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.85 out of 5 average rating, 81 reviews
Superhost
Townhouse in Oakland
Lakefront w Dock/Fire Pit, Walk to Honi/Uno
3 bedrooms, 4 beds, 3 bathrooms
25–30 Jul
New place to stay
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 92 reviews