A serene lake with a reflection of a forested mountain and a small house on the shore.

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Winston bed & breakfast

Front of property

1. Historical John Rast House

Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (52 reviews)
"We loved the atmosphere of the historic home and getting to know our hosts who were tremendous when we asked them for providing recommendations on places we might visit in the area. This was one of the best places that we stayed at during our vacation."
United States
Michael
The price is AED 420
AED 570 total
includes taxes & fees
9 Aug - 10 Aug
Historical John Rast House
Porch

2. C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (20 reviews)
"Clean and beautiful house, the host is very nice and kind."
United States
Kuan-Ju
The price is AED 682
AED 692 total
includes taxes & fees
11 Aug - 12 Aug
C.H. Bailey House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winston Hotel Reviews

Riverfront Inn Roseburg

Riverfront Inn Roseburg

8/10 Good
"A unique little piece of property that is well maintained. The staff was friendly and helpful."
Denis 1-night trip
Posted less than an hour ago
Riverfront Inn Roseburg

Frequently asked questions

Searching for B&Bs in Winston?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're a solo traveler hoping to get some local recommendations, B&Bs can be a great choice for many types of vacationers. When you want to explore some attractions in town, Wildlife Safari and South Umpqua River are worth a stop.
Are you thinking about a B&B for your stay?
Every B&B has a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a home away from home.
What are the best bed and breakfasts in Winston?
Here are some well-liked B&Bs in the area: C.H. Bailey House: 5 rooms. 8.9 mi (14.3 km) from the heart of Winston. Enjoy the free full breakfast and hot tub. Historical John Rast House: 3 rooms. 7.1 mi (11.5 km) from the downtown core.
When should I book my B&B in Winston?
When you're planning your stay in Winston, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July with an average temp of 62°F, while the coldest months are December and February with an average of 40°F. Average annual precipitation for Winston is 48 inches.
What is there to do in Winston?
When you want to check out some attractions in town, you might consider a visit to Wildlife Safari and South Umpqua River. You might check out Abacela Winery if you have time to see more of the area.

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