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.

Find a Bed and Breakfast in Winchester from CA $303

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Winchester bed & breakfast

Interior

1. Artistic Lodging Queen suite

Artistic Lodging Queen suite
Paris
9.0 out of 10, Wonderful, (50 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
Artistic Lodging Queen suite
Building design

2. Chez Lyndon Manor

Chez Lyndon Manor
3.0 star property
Northside District
9.6 out of 10, Exceptional, (133 reviews)
"Great place to stay."
United States
Kevin
The price is CA $253
CA $303 total
includes taxes & fees
Aug 11 - Aug 12
Chez Lyndon Manor
Interior

3. Artistic Lodging King Suite

Artistic Lodging King Suite
Paris
9.2 out of 10, Wonderful, (70 reviews)
"We were just passing through the area but this was a lovely stay, very comfortable and cute, and very clean!"
United States
Sarah E.
Artistic Lodging King Suite
Pool

4. 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.
The price is CA $252
CA $314 total
includes taxes & fees
Aug 7 - Aug 8
Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2
Pool

5. 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
The price is CA $252
CA $314 total
includes taxes & fees
Aug 7 - Aug 8
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

Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"Large room for our toddler to run around but sadly the carpet turned her feet/socks black. The shower head was also nearly impossible to fully turn off which explains the rust on the drain."
Daniel 1-night trip
Posted 3 hours ago
Hyatt Place Lexington

Find out more about Winchester

Winchester B&B information

Number of reviews
254
Accommodation
7 B&B
Lowest Price
CA $303
Highest Price
CA $314

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're passing through town and are looking for an accommodation that's small and charming, or you're traveling solo and hoping to make some connections, B&Bs can be a great choice for many travelers. While you're enjoying your trip to Winchester, Wiseman Park and Winchester Traveling Trail are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is a good option for you?
With attentive service, opportunities to mingle with other guests, and of course a scrumptious breakfast, B&Bs provide a one-of-a-kind setting.
What are the best B&Bs in Winchester?
Check out this B&B in the surrounding area: Chez Lyndon Manor: 7 rooms. 17.5 mi (28.2 km) from the downtown core. Enjoy the free cooked breakfast and outdoor tennis.
When is the best time to book my B&B in Winchester?
When you're planning your escape 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 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Wiseman Park and Winchester Traveling Trail are some notable spots. You might put Bluegrass Heritage Museum and Winchester Opera House on your list if you want to see more of the area.
How can I get to and around Winchester?
You can map out your trip in and around Winchester ahead of time with these transportation options. Fly into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) away from the heart of the city. If you'd like to explore around the area, consider renting a car to take in more sights.

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