Book Winchester Bed & Breakfast

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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, (73 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
$113 nightly
The price is $125
Nov 15 - Nov 16
Total with taxes and fees
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
$236 nightly
The price is $274
Nov 16 - Nov 17
Total with taxes and fees
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.
$100 nightly
The price is $110
Nov 24 - Nov 25
Total with taxes and fees
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.
$196 nightly
The price is $216
Nov 15 - Nov 16
Total with taxes and fees
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
$218 nightly
The price is $240
Nov 15 - Nov 16
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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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

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 $109 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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