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Check prices for these dates

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

Our top choices for Winchester 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
$158 nightly
The price is $170
Aug 9 - Aug 10
Total with taxes and fees
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
$206 nightly
The price is $209
Aug 11 - Aug 12
Total with taxes and fees
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 Winchester Hotel Reviews

SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

10/10 Excellent
"The staff was excellent and helpful - but this is an aging facility."
Christopher 1-night trip
Posted 18 hours ago
SureStay by Best Western Roseburg

Find out more about Winchester

Winchester B&B information

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 B&B
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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 Winchester Dam or Melrose Vineyards if you have time to see more of the area.

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