Book Winchester Bed & Breakfast

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

Other property types in Winchester

Property grounds
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
9.8 out of 10, Exceptional, (43)
"The place is really comfortable, and the trails and nature around are perfect for exploring, especially with my dog. It was so easy to relax and just enjoy the quiet. Great spot if you want a break from it all and don’t want to worry about leaving your pet behind. Definitely recommend!"
The price is $97
$123 total
includes taxes & fees
May 29 - May 30
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Property grounds
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
9.8 out of 10, Exceptional, (66)
"Beautiful, spacious and delightful"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Exterior
Home with great location
10.0 out of 10, Exceptional, (9)
"Loved the property. Perfect place for our family while attending our daughter’s graduation. Conveniently located. House is so quaint. Highly recommend it."
Home with great location
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.

Winchester B&B information

Number of reviews
12
Accommodation
2 B&B
Lowest Price
$239
Highest Price
$260

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find an accommodation with fewer rooms than a hotel and an intimate environment, a bed and breakfast might be just the right fit for your vacation to Winchester.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to interact with the owner, and tasty breakfasts, B&Bs offer a unique setting.
What are the best bed and breakfasts in Winchester?
Here are some B&Bs in the area: Villa DeWolf: 4 rooms. 13.5 mi (21.8 km) from the heart of Winchester. Enjoy the free cooked breakfast and designer toiletries. Blessings on State Bed & Breakfast: 2 rooms. 13.3 mi (21.4 km) from the downtown core. Enjoy the designer toiletries and spa.
When should I stay at a B&B in Winchester?
When you’re dreaming of a trip to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°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 Jacksonville Community Park. Morgan County Fairgrounds and Lake Jacksonville are also some sites to visit if you want to see more of the area.

Recent reviews of Winchester hotels
Expedia verified reviews

William Watson Hotel

William Watson Hotel

5/5 Excellent
Truly the best!
"I have booked over 100 rooms through Hotels.com…this room was the best ever! Everything was amazing. Clean, comfortable bed, great old world ambience, and lots of space to spread out! I will definitely be staying here again!"
A verified traveler stayed at William Watson Hotel
Posted 5 days ago
William Watson Hotel