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Search results; 219 homes in Winston

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Guest favourite
Home in Winston
Twin palms
7 bedrooms, 9 beds, 5 private bathrooms
2–7 Oct
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4.9 out of 5 average rating, 122 reviews
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Top guest favourite
Home in Winston
Safari Retreat
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Winston
The Watusi Place - A Modern Umpqua Valley Getaway
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.98 out of 5 average rating, 234 reviews
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Home in Winston
The Winston House | Near Wildlife Safari
3 bedrooms, 5 beds, 1 bathroom
18–23 Sept
New place to stay
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Guest favourite
Home in Winston
Family-Friendly Winston Vacation Rental w/ Deck!
4 bedrooms, 5 beds, 2 bathrooms
8–13 Nov
4.88 out of 5 average rating, 41 reviews
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Farm stay in Winston
Humble House on the horse ranch
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.62 out of 5 average rating, 171 reviews
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Top guest favourite
Guest house in Winston
Big Rock Bunk House
1 bedroom, 1 bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 47 reviews
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Guest house in Winston
The Harvest Studio
1 bedroom, 1 bed, 1 bathroom
18–23 Sept
New place to stay
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Top guest favourite
Cottage in Tenmile
The Cottages at Porter Hill (Green)-Near Roseburg
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 170 reviews
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Top guest favourite
Home in Roseburg
Country View Retreat-3 BD 2 BA & Outdoor Seating
3 bedrooms, 3 beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Roseburg
The Dr. J. R. Chapman Home
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 268 reviews
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Guest favourite
Home in Roseburg
Xenia House-Valley View
4 bedrooms, 6 beds, 2.5 bathrooms
26–31 Oct
4.93 out of 5 average rating, 96 reviews
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Superhost
Home in Days Creek
The Lookout&CrowsNest Retreat at Pachamama Farm
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
New place to stay
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Home in Roseburg
River House at Rising River
3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Sept
4.81 out of 5 average rating, 16 reviews
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Top guest favourite
Treehouse in Sutherlin
Mountain View Treehouse
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 146 reviews
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Farm stay in Dillard
Nancy’s Dahlia farm
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Sept
4.55 out of 5 average rating, 40 reviews
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Top guest favourite
Guest house in Glide
Steelhead Guest House W/Game Room
1 bedroom, 3 beds, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 140 reviews
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Top guest favourite
Home in Riddle
Cinder Cottage ~ No Cleaning Fee
2 bedrooms, 2 queen beds, 1 bathroom
28 Sept – 3 Oct
4.94 out of 5 average rating, 299 reviews
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Top guest favourite
Guest suite in Roseburg
Umpqua Valley Garden Getaway
1 king bed, 1 bathroom
3–8 Nov
4.98 out of 5 average rating, 321 reviews