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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 2 B&B in Winchester with updated reviews, rates, and availability.

Charming Historic lodge across from Umpqua river
Interior detail

Charming Historic lodge across from Umpqua river

10.0 out of 10, Exceptional, (23)
"The room was clean. John and Joanne are lovely people and the bana bread was wonderful!"
The price is SAR 375
SAR 457 total
includes taxes & fees
14 Feb - 15 Feb
Charming Historic lodge across from Umpqua river
Historical John Rast House
Room

Historical John Rast House

3.0 star property
10.0 out of 10, Exceptional, (34)
"great stay"
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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Other property types in Winchester

Singing Waters at N. Umpqua
View of river from back deck

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (5)
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"
Singing Waters at N. Umpqua
Firewater Lodge Cabin Experience
Exterior

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (47)
"We are repeat renters and thoroughly enjoy our home away from home every year. Thank you!"
Firewater Lodge Cabin Experience
Family-Friendly Winston Vacation Rental w/ Deck!
Winston Vacation Rental | 4BR | 2BA | Stairs Required | 1,704 Sq Ft

Family-Friendly Winston Vacation Rental w/ Deck!

9.8 out of 10, Exceptional, (10)
"Rooms are spacious and each have their own controller for heat or air conditioning so you can keep the room temp to your liking. The deck is huge and perfect for hanging outside even in wet weather because it’s totally covered. Nice fully stocked kitchen with a variety of appliances and kitchen utensils. The nice surprise was the garage with the ping pong table and work out equipment. They also provide a stroller high chair and pak n play if you have a baby"
Family-Friendly Winston Vacation Rental w/ Deck!
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.

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?
Check out this B&B in the surrounding area: 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 Melrose Vineyards or Reustle Prayer Rock Vineyards if you have time to see more of the area.