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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!"
$275 nightly
The price is $313
Aug 7 - Aug 8
Total includes taxes and fees
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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Top Winchester Hotel Reviews

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Nice comfortable place and close to family "
Robert 1-night trip
Posted 1 day ago
William Watson Hotel

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $313 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant month of September when the summer crowds have dispersed, yet the weather remains pleasantly warm. This transitional period allows visitors to enjoy outdoor activities such as hiking the scenic trails of the Shenandoah National Park and exploring the historic downtown area without the hustle and bustle of peak tourist season.

From May through July, Winchester experiences its peak season, drawing in travelers who are eager to explore the region's rich history and beautiful landscapes. During these months, temperatures can range from the mid-60s to the high 80s Fahrenheit, making it ideal for outdoor sightseeing and festivals. The area comes alive with various events, including local fairs and outdoor concerts, providing an exciting atmosphere for those who thrive on social engagement.

For those looking for a more budget-friendly experience, November is a fantastic option. The fall foliage creates a stunning backdrop for leisurely walks and photography, and the area tends to be quieter, allowing for a more intimate exploration of Winchester's charming sites and attractions. With fewer tourists, you can enjoy a more personalized experience at local restaurants and shops.
What is the difference between a Winchester B&B and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.