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 $315

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Winchester bed & breakfast

Building design

Chez Lyndon Manor

Chez Lyndon Manor
3.0 star property
Northside District
9.6 out of 10, Exceptional, (130 reviews)
"Great place to stay."
United States
Kevin
The price is CA $263
CA $315 total
includes taxes & fees
Jun 22 - Jun 23
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.
The price is CA $255
CA $318 total
includes taxes & fees
Jun 22 - Jun 23
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
The price is CA $255
CA $318 total
includes taxes & fees
Jun 22 - Jun 23
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

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"Beautiful place to stay. Breakfast bar is full of everything you would ever want to eat for breakfast!"
Tammie 1-night trip
Posted 1 hour ago
Marriott Lexington Griffin Gate Golf Resort & Spa

Find out more about Winchester

Winchester B&B information

Number of reviews
131
Accommodation
7 B&B
Lowest Price
CA $315
Highest Price
CA $321

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, Community Park and The Holler 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 heart of Winchester. 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, Community Park and The Holler are some notable spots. You might put Bluegrass Heritage Museum and Wiseman Park 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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