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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

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, (7)
"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 AED 1,010
AED 1,151 total
includes taxes & fees
3 Apr - 4 Apr
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

The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (53)
"We had an overnight stay during a very long roadtrip, the loft was perfect and we were able to have a very relaxing night after eating some of the best pizza I have ever had, highly recommend the place just a few hundred feet away. Communication with owners was perfect."
The price is AED 312
AED 569 total
includes taxes & fees
6 Apr - 7 Apr
The Farmhouse Loft "Greene County's Guesthouse"
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Property grounds

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

9.8 out of 10, Exceptional, (50)
"I had such a great stay here with my dogs. The place had everything we needed and then some. The property is beautiful and I was lucky the weather cooperated so we could walk through the trails and I could take some pictures of the many birds in the area. I will definitely be back. Thank you!"
The price is AED 404
AED 502 total
includes taxes & fees
3 Apr - 4 Apr
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
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, (21)
"We had a great stay. The environment is just cuddling. "
The price is AED 349
AED 443 total
includes taxes & fees
3 Apr - 4 Apr
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.