Book Winchester Bed & Breakfast

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Our top choices for Winchester bed & breakfast

C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (6 reviews)
"The personal service was awesome. Loved the hot tub. Wish we could of stayed longer!"
United States
David
$194 nightly
The price is $197
Apr 29 - Apr 30
Total with taxes and fees
C.H. Bailey House

Historical John Rast House

Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (49 reviews)
"When you find yourself in Roseburg, have an interest in local history and tired of the corporate cookie-cutter hotel options, choose the John Rast House. You will experience a warm welcome, delicious breakfast and spotless, comfortable accommodations all within a past period atmosphere. "
United States
Barbara
$179 nightly
The price is $193
Apr 28 - Apr 29
Total with taxes and fees
Historical John Rast House

1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River

1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River
Glide
$110 nightly
The price is $112
Apr 28 - Apr 29
Total with taxes and fees
1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River
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

Find out more about Winchester

Winchester B&B information

Number of reviews
55
Accommodation
2 B&B
Lowest Price
$112
Highest Price
$197

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. 1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River: 17.1 mi (27.6 km) from the heart of downtown.
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 Reustle Prayer Rock Vineyards if you have time to see more of the area.

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