Search B&B in Winchester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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, (6)
"What a truly beautiful place for a quick getaway. The owner went out of his way to ensure that we felt at home and welcomed. In addition to the ambiance of setting, the owner prepared a delicious breakfast of blueberry pancakes, bacon and fruit. We couldn’t ask for a better stay and we will make sure that we stay again during our next trip to Chicago ❤️"
The price is AED 1,010
AED 1,136 total
includes taxes & fees
14 Nov - 15 Nov
Villa DeWolf
Blessings on State Bed & Breakfast
Front of property
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. "
The price is AED 878
AED 988 total
includes taxes & fees
22 Nov - 23 Nov
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

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Summertime
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (49)
"The house was great and the people were very nice and helpful. "
The price is AED 716
AED 815 total
includes taxes & fees
2 Dec - 3 Dec
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Art Themed Loft Apartment in Jacksonville
Living area
Art Themed Loft Apartment in Jacksonville
9.6 out of 10, Exceptional, (5)
"So cutely decorated! Much bigger than expected. Would definitely stay here again."
The price is AED 349
AED 549 total
includes taxes & fees
14 Nov - 15 Nov
Art Themed Loft Apartment in Jacksonville
Home with great location
Exterior
Home with great location
10.0 out of 10, Exceptional, (15)
"Such a wonderful home. The decor is charming. Great location"
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.

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.