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Check prices for these dates

Next weekend
Mar 20 - Mar 22
In two weeks
Mar 27 - Mar 29
In one month
Apr 10 - Apr 12
In two months
May 8 - May 10

Our top choices for Winchester bed & breakfast

Porch

C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Gorgeous setting. Lovely and exceptionally clean room - the bed was SO comfy. Really nice little touches too by the host, who was friendly and made us a great breakfast. Wish we could have stayed longer to explore the area."
United States
Alice
$160 nightly
The price is $163
Mar 13 - Mar 14
Total with taxes and fees
C.H. Bailey House
Front of property

Historical John Rast House

Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (49 reviews)
"Loved this stay!"
United States
Rosemary
$179 nightly
The price is $193
Mar 19 - Mar 20
Total with taxes and fees
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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Top Winchester Hotel Reviews

Comfort Inn Roseburg

Comfort Inn Roseburg

10/10 Excellent
"Comfortable"
Ronald 2-night trip
Posted 9 hours ago
Comfort Inn Roseburg

Find out more about Winchester

Winchester B&B information

Number of reviews
51
Accommodation
3 B&B
Lowest Price
$163
Highest Price
$193

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than the traditional hotel and a more personalized environment, a B&B might be a great fit for your vacation to Winchester. When you want to explore some of the destination's attractions, North Umpqua River is worth a visit.
Why should you consider B&Bs instead of traditional hotels?
B&Bs all have a unique charm. Whether it's a comfy common area with a fireplace 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 top B&Bs in Winchester?
Here are some B&Bs in the surrounding area: C.H. Bailey House: 5 rooms. 9.7 mi (15.6 km) from the heart of Winchester. Enjoy the free full breakfast and hot tub. Historical John Rast House: 3 rooms. 4.7 mi (7.5 km) from the downtown core.
When is the best time to book my B&B in Winchester?
When you're dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 64°F, while the coldest months are December and February with an average of 41°F. Average annual precipitation for Winchester is 49 inches.
What is there to do in Winchester?
If you want to check out some popular attractions in Winchester, you might enjoy a visit to North Umpqua River. You might also consider a trip to sites like Melrose Vineyards or Douglas County Museum of History and Natural History if you have time to see more of the area.

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