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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured B&B in Winchester

Villa DeWolf
Front of property

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (10)
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
Villa DeWolf
Blessings on State Bed & Breakfast
Property grounds

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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Frequently asked questions

Searching for B&Bs in Winchester?
If you're looking for a place to stay with fewer rooms than a hotel and an intimate environment, a bed and breakfast might be a great fit for your getaway to Winchester.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to meet guests from other places and of course a full breakfast to start the day, B&Bs provide a one-of-a-kind 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 city centre. Enjoy the designer toiletries and spa.
When is the best time to stay at a B&B in Winchester?
When you're dreaming of a getaway to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.
What is there to do in Winchester?
If you want to see 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.