Search B&B in Winchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

Villa DeWolf
Front of property

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (8)
"The owner, Jethro DeWolfe, met us and showed us all the rooms in this pre-Civil War era mansion and gave us quite a tour and explained much of the home’s restoration, contents and history. Great place."
The price is SAR 1,031
SAR 1,175 total
includes taxes & fees
5 May - 6 May
Villa DeWolf
Blessings on State Bed & Breakfast
Porch

Blessings on State Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (55)
"Excellent property with welcoming staff and cozy, well-appointed rooms. "
Blessings on State Bed & Breakfast
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Interior

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10.0 out of 10, Exceptional, (3)
"Absolutely loved our stay! Comfortable and cozy! Felt like we were staying in the Ingalls little house, but with modern conveniences. It really was a hidden gem! Can’t recommend enough! My only feedback is that the master bed wasn’t super comfy. Great stay and great host"
The price is SAR 484
SAR 589 total
includes taxes & fees
5 May - 6 May
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Aerial view

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10.0 out of 10, Exceptional, (5)
"Perfect spot for my spouse and I for an overnight stay. Clean and comfortable and just on the outskirts of town. We appreciated and loved the surprise coffee cake! "
The price is SAR 334
SAR 429 total
includes taxes & fees
18 May - 19 May
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Fridge, microwave, oven, stovetop

Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

10.0 out of 10, Exceptional, (23)
"Great spot for our weekend away!"
The price is SAR 285
SAR 377 total
includes taxes & fees
5 May - 6 May
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
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 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.