An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Winchester bed & breakfast

Interior

Artistic Lodging Queen suite

Artistic Lodging Queen suite
Paris
9.2 out of 10, Wonderful, (48 reviews)
"Room was very nice, comfortable and clean. Neighborhood quiet. Very easy walking distance to the area attractions and good dining options. Didn't partake of breakfast, went to a nearby cafe that we'd already decided to go to. A very nice stay."
United States
Debra
$108 nightly
The price is $119
Jul 19 - Jul 20
Total with taxes and fees
Artistic Lodging Queen suite
Building design

Chez Lyndon Manor

Chez Lyndon Manor
3.0 star property
Northside District
9.6 out of 10, Exceptional, (132 reviews)
"Great place to stay."
United States
Kevin
$186 nightly
The price is $216
Jul 21 - Jul 22
Total with taxes and fees
Chez Lyndon Manor
Pool

Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2

Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2
Irvine
10.0 out of 10, Exceptional, (1 review)
"The house was beautiful! Parts of it were built in 1880 with very high ceilings. The kitchen was modern. The pool was very clean and the pool area was really nice. Our hosts very kind and accomodating. We might stay with them next summer."
United States
Niki T.
$206 nightly
The price is $227
Jul 19 - Jul 20
Total with taxes and fees
Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2
Pool

Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 3

Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 3
Irvine
$206 nightly
The price is $227
Jul 19 - Jul 20
Total with taxes and fees
Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 3
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

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

8/10 Good
"A good affordable overnight stop. Could use some updating and cleaning in the hallways. Maintenance needed on ceiling tiles. Staff was very kind and helpful."
Michele 1-night trip
Posted 4 hours ago
Quality Inn Lexington -Horse Park

Find out more about Winchester

Winchester B&B information

Number of reviews
181
Accommodation
6 B&B
Lowest Price
$119
Highest Price
$227

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.

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