Find a Bed and Breakfast in Winchester from CA $242

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Check prices for these dates

Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5

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, (1 review)
The price is CA $367
CA $373 total
includes taxes & fees
Feb 24 - Feb 25
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, (48 reviews)
"Loved this stay!"
United States
Rosemary
The price is CA $183
CA $242 total
includes taxes & fees
Mar 8 - Mar 9
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

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

10/10 Excellent
"Yes it was perfect"
Matthew 2-night trip
Posted 5 days ago
Motel 6 Roseburg, OR

Find out more about Winchester

Winchester B&B information

Number of reviews
49
Accommodation
3 B&B
Lowest Price
CA $242
Highest Price
CA $373

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 Reustle Prayer Rock Vineyards if you have time to see more of the area.

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