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Search results; 215 homes in Winston

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Top guest favourite
Guest house in Winston
Big Rock Bunk House
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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5.0 out of 5 average rating, 43 reviews
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Home in Winston
Safari Retreat
3 bedrooms, 5 beds
6–11 Sept
4.98 out of 5 average rating, 54 reviews
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Home in Winston
The Watusi Place - A Modern Umpqua Valley Getaway
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 232 reviews
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Cabin in Winston
Rustic cabin in the woods
1 bedroom, 3 beds
1–6 Sept
5.0 out of 5 average rating, 58 reviews
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Home in Winston
Family-Friendly Winston Vacation Rental w/ Deck!
4 bedrooms, 5 beds
1–6 Nov
4.88 out of 5 average rating, 40 reviews
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Home in Winston
Twin palms
7 bedrooms, 9 beds
30 Sept – 5 Oct
4.91 out of 5 average rating, 119 reviews
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Home in Roseburg
Country View Retreat-3 BD 2 BA & Outdoor Seating
3 bedrooms, 3 beds
17–22 Oct
5.0 out of 5 average rating, 10 reviews
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Home in Roseburg
Farmhouse By the Sea
2 bedrooms, 2 beds
1–6 Sept
5.0 out of 5 average rating, 57 reviews
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Home in Roseburg
Xenia House-Valley View
4 bedrooms, 6 beds
26–31 Oct
4.93 out of 5 average rating, 95 reviews
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Camper van/Motorhome in Roseburg
Chic RV Retreat, Stunning Yard in Roseburg
2 bedrooms, 4 beds
1–6 Sept
4.98 out of 5 average rating, 143 reviews
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Farm stay in Winston
Humble House on the horse ranch
2 bedrooms, 2 beds
13–18 Sept
4.62 out of 5 average rating, 171 reviews
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Home in Roseburg
Comforts of home in quiet area.
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 44 reviews
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Guest house in Winston
The Harvest Studio
1 bedroom, 1 bed
1–6 Sept
New place to stay
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Farm stay in Dillard
Nancy’s Dahlia farm
2 bedrooms, 2 queen beds
1–6 Sept
4.63 out of 5 average rating, 38 reviews
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Cabin in Days Creek
Creekside cabin at Pachamama Farm
2 bedrooms, 3 beds
10–15 Sept
4.87 out of 5 average rating, 183 reviews
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Home in Roseburg
Cozy downtown retreat with two living quarters
3 bedrooms, 4 beds
12–17 Sept
4.93 out of 5 average rating, 45 reviews
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Home in Roseburg
A Restful Studio Near a Creek and Forest - Pets
2 beds
12–17 Oct
5.0 out of 5 average rating, 260 reviews
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Room in Roseburg
Private room in PNW
1 queen bed
7–12 Sept
4.94 out of 5 average rating, 34 reviews
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Home in Roseburg
1917 Cabin on working Lavender Farm
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 51 reviews