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Search results; Over 1,000 homes in Oakland

Top guest favourite
Tiny home in Oakland
Lil' Sumpin
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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5.0 out of 5 average rating, 82 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 175 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Aug
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.9 out of 5 average rating, 105 reviews, 5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 89 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Oakland
Molly
4.99 out of 5 average rating, 168 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Oakland
The Other House
4.95 out of 5 average rating, 20 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Aug
Guest favourite
Home in Oakland
Cottage on Jericho Road
4.78 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
4.82 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Nov – 3 Dec
Home in Terra Alta
NEW Golden Hour Getaway at Alpine Lake
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 5 beds, 4.5 bathrooms
1–6 Aug
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 208 reviews, 2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Superhost
Hotel room in Oakland
Cove Creek Lodge: 202 Poolside Double Queen Room
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 42 reviews, 1 bed, 1 bathroom
18–23 Aug
Top guest favourite
Barn in Oakland
Couples Retreat: The HayLoft- Rustic Escape For 2
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
4.9 out of 5 average rating, 84 reviews, 2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
4.97 out of 5 average rating, 112 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Oakland
Lucy’s Lookout
4.83 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
4.98 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Aug
Top guest favourite
Home in Oakland
The Little Fox Den *Lake View*
4.95 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug