Search B&B in Winchester

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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

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 1,009
AED 1,151 total
includes taxes & fees
2 Mar - 3 Mar
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.
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Other property types in Winchester

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Terrace/patio

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

9.8 out of 10, Exceptional, (71)
"Thanks for having us"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
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, (2)
"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 AED 327
AED 421 total
includes taxes & fees
16 Mar - 17 Mar
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Fridge, microwave, oven, stovetop

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (50)
"We stayed a few nights. House is clean and in very good shape. People are very nice and easy to work with."
The price is AED 716
AED 797 total
includes taxes & fees
8 Mar - 9 Mar
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
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.