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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 5 B&B in Winchester with updated reviews, rates, and availability.

Lyndon House B&B
Interior detail

Lyndon House B&B

3.0 star property
9.6 out of 10, Exceptional, (111)
"Lovely people, beautifully renovated property in an excellent location in Lexington."
$226 nightly
The price is $262
Jun 25 - Jun 26
Total includes taxes and fees
Lyndon House B&B
Artistic Lodging Queen suite
Interior

Artistic Lodging Queen suite

9.2 out of 10, Wonderful, (42)
"Very neat and clean, close to everything we wanted!"
$108 nightly
The price is $119
Jun 25 - Jun 26
Total includes taxes and fees
Artistic Lodging Queen suite
The Guesthouse at Rosecrest Farm
Exterior

The Guesthouse at Rosecrest Farm

3.0 star property
10.0 out of 10, Exceptional, (18)
"Fantastic setting and accommodations Breakfast was delicious."
The Guesthouse at Rosecrest Farm
Artistic Lodging King Suite
Shower, hair dryer, towels, soap

Artistic Lodging King Suite

9.2 out of 10, Wonderful, (70)
"We were just passing through the area but this was a lovely stay, very comfortable and cute, and very clean!"
$121 nightly
The price is $133
Jun 30 - Jul 1
Total includes taxes and fees
Artistic Lodging King Suite
Chateau Annette
Suite, 1 King Bed (Dream Suite) | Free cribs/infant beds, free wired internet

Chateau Annette

3.5 star property
10.0 out of 10, Exceptional, (11)
Chateau Annette
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

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 $119 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 peak season from July to September, when the town comes alive with vibrant activities and picturesque landscapes. This period is particularly attractive for travelers who enjoy outdoor exploration, as you'll find great conditions for hiking and sightseeing amidst the stunning scenery of the surrounding countryside.
July, the most popular month, offers warm temperatures that typically range from the mid-70s to low 90s Fahrenheit, making it ideal for outdoor festivals and events. Visitors can immerse themselves in Winchester's rich history, with opportunities to explore historic sites and enjoy local cuisine at outdoor markets.
If you're looking for a quieter experience, consider visiting in November. This month allows you to appreciate the beauty of Winchester without the crowds, and you might discover charming local shops and cozy cafés that provide a warm respite from the autumn chill. Plus, you can still enjoy the area's natural beauty as the foliage transforms into vibrant colors.
What is the difference between a Winchester Bed & Breakfast 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.