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Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec

Our top choices for Winchester bed & breakfast

A two-story house with a porch, a flag, and a sign indicating it is for sale.

1. Historical John Rast House

Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (53 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
The price is HK$1,052
HK$1,388 total
includes taxes & fees
20 Oct - 21 Oct
Historical John Rast House
A glass table with wine glasses and a decorative bowl, set on a patio with a view of hills and a sofa with colorful cushions.

2. C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (30 reviews)
"Comfortable room, great breakfast and we loved the bocce ball court!"
United States
RaShel
The price is HK$1,423
HK$1,445 total
includes taxes & fees
1 Nov - 2 Nov
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

The Ranch Motel

The Ranch Motel

10/10 Excellent
"Perfect two-night stay for the lady and me. Cozy like A-frame-style homes with a vintage feel. Staff was amazing and tended to anything in need."
Brayden 2-night trip
Posted 4 hours ago
The Ranch Motel

Find out more about Winchester

Winchester B&B information

Number of reviews
83
Accommodation
2 B&B
Lowest Price
HK$1,388
Highest Price
HK$1,445

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a more personalised environment, a B&B might be just the right fit for your trip to Winchester. When you want to explore some of the destination's attractions, North Umpqua River is worth a visit.
Why would you choose B&Bs instead of traditional hotels?
Every B&B has its own unique feel — whether it's a garden for guests to admire or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a fun place to get away.
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 city centre.
What's the best time of year to book my B&B in Winchester?
When you're dreaming of a escape to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and February, with an average of 5°C. Average annual precipitation for Winchester is 1255 mm.
What is there to do in Winchester?
If you want to see some popular attractions in Winchester, you might enjoy a visit to North Umpqua River. You might also consider a trip to sites such as Stewart Park or Melrose Vineyards if you have time to see more of the area.

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