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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

B&B in Winchester

Interior
Charming Historic lodge across from Umpqua river

Charming Historic lodge across from Umpqua river

Glide
10.0 out of 10, Exceptional, (35)
"Beautiful property and great to deal with. Loved our stay"
United States
Joe
The price is SAR 375
SAR 457 total
includes taxes & fees
25 Nov - 26 Nov
Charming Historic lodge across from Umpqua river
Outdoor spa tub
C.H. Bailey House

C.H. Bailey House

2.0 star property
Roseburg
The price is SAR 952
SAR 966 total
includes taxes & fees
1 Dec - 2 Dec
C.H. Bailey House
Lobby sitting area
Historical John Rast House

Historical John Rast House

3.0 star property
Roseburg
10.0 out of 10, Exceptional, (48)
"So glad we stayed here! The house was amazing if you like history. Our hosts were wonderful, breakfast was delicious and downtown is a short walk away. The property is gated and felt very safe. "
United States
Jessica
The price is SAR 503
SAR 663 total
includes taxes & fees
4 Dec - 5 Dec
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

SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

10/10 Excellent
"Very large room, fantastic breakfast, and kind staff!"
Heather 2-night trip
Posted 2 days ago
SureStay by Best Western Roseburg

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. Charming Historic lodge across from Umpqua river: 17.1 mi (27.5 km) from the downtown core. Historical John Rast House: 3 rooms. Situated 4.7 mi (7.5 km) from the heart of Winchester.
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 Stewart Park or Melrose Vineyards if you have time to see more of the area.