Find a Bed and Breakfast in Winchester from CA $105

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Winchester bed & breakfast

A room with two upholstered chairs, a small table with a lamp, and a view through a window with a decorative glass design.

1. Artistic Lodging King Suite

Artistic Lodging King Suite
Paris
9.2 out of 10, Wonderful, (72 reviews)
"Got the information needed in plenty of time prior to arrival. Bedroom & bath were clean. Be sure to take own body soap/gel, shampoo & conditioner. Kitchen well supplied with coffee, tea & snacks. Convenient location to downtown Paris. Thankfully a place that doesn’t allow pets!"
United States
Stephanie
The price is CA $114
CA $176 total
includes taxes & fees
Nov 15 - Nov 16
Artistic Lodging King Suite
A grand entryway with a wooden staircase, a chandelier, and a view of a cozy living room with a sofa and lamps.

2. Chez Lyndon Manor

Chez Lyndon Manor
3.0 star property
Northside District
9.6 out of 10, Exceptional, (135 reviews)
"Wonderful location and lovely B&B."
United States
Barbara
The price is CA $323
CA $387 total
includes taxes & fees
Nov 16 - Nov 17
Chez Lyndon Manor
A room with two upholstered chairs, a small table with a lamp, and a view through a window with a decorative glass design.

3. Artistic Lodging Queen suite

Artistic Lodging Queen suite
Paris
9.0 out of 10, Wonderful, (51 reviews)
"The room was not ready at 6:30 PM and the cleaning person asked us to come back a couple hours later. I still have not heard from the host, they never reached out with check in information or to address the room condition. We ended up at a hotel for the night. 10/10 do NOT recommend."
United States
Missy B.
The price is CA $106
CA $167 total
includes taxes & fees
Nov 24 - Nov 25
Artistic Lodging Queen suite
A rectangular swimming pool with a white deck and a slide, surrounded by a wooden fence.

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 $254
CA $305 total
includes taxes & fees
Nov 21 - Nov 22
Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2
A rectangular swimming pool with a white deck and a slide, surrounded by a wooden fence.

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 $282
CA $339 total
includes taxes & fees
Nov 21 - Nov 22
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.
View all properties

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
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.

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, College Park and GRCHS Baseball Field 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, College Park and GRCHS Baseball Field are some notable spots. You might put Bluegrass Heritage Museum and Cassell Creek Golf Course 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.

Explore a world of travel with Expedia