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Search results; 214 homes in Winston

Guest favourite
Home in Winston
Twin palms
7 bedrooms, 9 beds, 5 private bathrooms
20–25 Aug
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4.91 out of 5 average rating, 119 reviews
Top guest favourite
Home in Winston
Safari Retreat
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Winston
Rustic cabin in the woods
1 bedroom, 3 beds, WC
17–22 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Winston
The Watusi Place - A Modern Umpqua Valley Getaway
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.98 out of 5 average rating, 231 reviews
Top guest favourite
Cottage in Tenmile
The Cottages at Porter Hill (Green)-Near Roseburg
1 bedroom, 1 queen bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 162 reviews
Top guest favourite
Guest house in Winston
Big Rock Bunk House
1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 41 reviews
Farm stay in Winston
Humble House on the horse ranch
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.63 out of 5 average rating, 170 reviews
Top guest favourite
Cottage in Tenmile
The Cottages at Porter Hill (Blue)-Near Roseburg
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 99 reviews
Guest favourite
Guest house in Roseburg
Private studio in safe quiet neighborhood
1 bedroom, 1 double bed, 1 bathroom
18–23 Aug
4.83 out of 5 average rating, 42 reviews
Guest favourite
Home in Winston
Family-Friendly Winston Vacation Rental w/ Deck!
4 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.87 out of 5 average rating, 38 reviews
Top guest favourite
Home in Roseburg
Country View Retreat-3 BD 2 BA & Outdoor Seating
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest house in Glide
Steelhead Guest House W/Game Room
1 bedroom, 3 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 119 reviews
Top guest favourite
Cabin in Roseburg
Lil Cedar Lodge
1 bedroom, 1 bed, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 58 reviews
Guest favourite
Farm stay in Roseburg
Winery stay get-away on secluded small farm
2 beds, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 6 reviews
Farm stay in Dillard
Nancy’s Dahlia farm
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Aug
4.67 out of 5 average rating, 36 reviews
Superhost
Guest house in Glide
Highway to Diamond Lake/Crater Lake roadtrip stop!
1 bedroom, 3 beds, 1 bathroom
12–17 Aug
4.89 out of 5 average rating, 266 reviews
Guest favourite
Tiny home in Roseburg
Forest Haven Tiny House
2 bedrooms, 2 beds, 1 bathroom
26–31 Aug
4.9 out of 5 average rating, 94 reviews
Home in Roseburg
Cozy & Comfortable 2- Bedroom Home
2 bedrooms, 3 beds, 1 bathroom
12–17 Aug
4.33 out of 5 average rating, 6 reviews
Top guest favourite
Home in Roseburg North
Xenia House - North Roseburg
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 58 reviews