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Search results; 216 homes in Winston

Top guest favourite
Home in Winston
The Watusi Place - A Modern Umpqua Valley Getaway
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Oct
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4.98 out of 5 average rating, 233 reviews
Top guest favourite
Home in Winston
Safari Retreat
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 55 reviews
Home in Winston
The Winston House | Near Wildlife Safari
3 bedrooms, 5 beds
13–18 Sept
New place to stay
Top guest favourite
Cabin in Winston
Rustic cabin in the woods
1 bedroom, 3 beds
15–20 Sept
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in Winston
Family-Friendly Winston Vacation Rental w/ Deck!
4 bedrooms, 5 beds
8–13 Nov
4.88 out of 5 average rating, 41 reviews
Top guest favourite
Guest house in Winston
Big Rock Bunk House
1 bedroom, 1 bed
12–17 Oct
5.0 out of 5 average rating, 46 reviews
Guest house in Winston
The Harvest Studio
1 bedroom, 1 bed
10–15 Sept
New place to stay
Farm stay in Dillard
Nancy’s Dahlia farm
2 bedrooms, 2 queen beds
8–13 Sept
4.64 out of 5 average rating, 39 reviews
Guest favourite
Home in Winston
Twin palms
7 bedrooms, 9 beds
30 Sept – 5 Oct
4.9 out of 5 average rating, 121 reviews
Guest favourite
Guest house in Roseburg
Aviation Suites: The Hangar Suite
1 bedroom, 1 bed
8–13 Sept
4.86 out of 5 average rating, 112 reviews
Top guest favourite
Cabin in Roseburg
*Riverfront* Log Cabin in Roseburg’s Wine Country
5 bedrooms, 8 beds
21–26 Sept
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Home in Roseburg
Cozy downtown retreat with two living quarters
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Home in Roseburg
Umpqua Riverfront Retreat |2 King Beds| Patio View
3 bedrooms, 4 beds
20–25 Sept
4.96 out of 5 average rating, 23 reviews
Guest favourite
Guest house in Winston
Peaceful Cottage Studio
1 bed
1–6 Jan
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Roseburg
The Bliss/100% privacy/AC/game room/2 blks 2 DT
2 beds
2–7 Nov
4.99 out of 5 average rating, 285 reviews
Top guest favourite
Cottage in Tenmile
The Cottages at Porter Hill (Green)-Near Roseburg
1 bedroom, 1 queen bed
12–17 Sept
5.0 out of 5 average rating, 168 reviews
Guest favourite
Home in Roseburg
Amazing Mid-Century Modern Home-Incredible Views!
3 bedrooms, 3 beds
10–15 Sept
4.9 out of 5 average rating, 70 reviews
Top guest favourite
Home in Roseburg
The Berd Haus | Quiet Mid-Century, Minutes Off I-5
3 bedrooms, 3 beds
21–26 Sept
4.96 out of 5 average rating, 165 reviews
Guest favourite
Home in Roseburg
Farmhouse By the Sea
2 bedrooms, 2 beds
21–26 Sept
5.0 out of 5 average rating, 58 reviews