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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bathroom
1–6 Aug
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4.97 out of 5 average rating, 229 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, 175 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.9 out of 5 average rating, 105 reviews
Top guest favourite
Cabin in Oakland
Molly
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.99 out of 5 average rating, 168 reviews
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.73 out of 5 average rating, 89 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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.78 out of 5 average rating, 18 reviews
Top guest favourite
Barn in Oakland
Couples Retreat: The HayLoft- Rustic Escape For 2
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 19 reviews
Home in Terra Alta
NEW Golden Hour Getaway at Alpine Lake
3 bedrooms, 5 beds, 4.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 112 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
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 161 reviews
Top guest favourite
Home in Oakland
The Little Fox Den *Lake View*
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.95 out of 5 average rating, 92 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
6–11 Aug
4.98 out of 5 average rating, 179 reviews
Superhost
Hotel room in Oakland
Cove Creek Lodge: 202 Poolside Double Queen Room
1 bedroom, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds, 1 bathroom
28 Nov – 3 Dec
4.82 out of 5 average rating, 84 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Aug
4.97 out of 5 average rating, 33 reviews