Find a Bed and Breakfast in Winston from CA $171

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Winston bed & breakfast

A glass table with wine glasses and a decorative bowl, set on a patio with a view of hills and a sofa with colorful cushions.

1. C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (31 reviews)
"Comfortable room, great breakfast and we loved the bocce ball court!"
United States
RaShel
The price is CA $231
CA $235 total
includes taxes & fees
Nov 14 - Nov 15
C.H. Bailey House
A two-story house with a porch, a flag, and a sign indicating it is for sale.

2. Historical John Rast House

Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (53 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 CA $171
CA $230 total
includes taxes & fees
Nov 14 - Nov 15
Historical John Rast 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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Learn more about Winston

Nestled along the South Umpqua River, this charming town invites visitors to drive through Wildlife Safari where lions and giraffes roam freely. Spend your afternoons exploring nearby vineyards like Abacela Winery or discovering local history at the Douglas County Museum just a short drive away.

See all hotels in Winston
A serene lake with a reflection of a forested mountain and a small house on the shore.

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, South Umpqua River and Wildlife Safari 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 South Umpqua River and Wildlife Safari. You might check out Abacela Winery if you have time to see more of the area.

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