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.

Bed and Breakfast in Winchester

  • 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
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 Aug

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
The price is NZ$210
includes taxes & fees
28 June - 29 June
Artistic Lodging Queen suite
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 NZ$394
includes taxes & fees
29 June - 30 June
Chez Lyndon Manor
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 NZ$400
includes taxes & fees
30 June - 1 July
Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 3
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 NZ$396
includes taxes & fees
28 June - 29 June
Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent
"Great bang for your buck . We stayed in the Lafayette suite and it was fantastic ."
Ashley 1-night trip
Posted 4 hours ago
DoubleTree Suites by Hilton Hotel Lexington

Find out more about Winchester

Winchester B&B information

Number of reviews
179
Accommodation
7 B&B
Lowest Price
NZ$210
Highest Price
NZ$400

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic holiday and are looking to stay somewhere quiet, or you're travelling solo and hoping to meet fellow tourists, a B&B can be a good choice for many different types of travellers. 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 the right choice for your stay?
With attentive service, opportunities to mingle with other guests and tasty breakfasts, B&Bs all have a truly one-of-a-kind setting.
What are the best B&Bs in Winchester?
Take a look at 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 should I 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 temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.
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 should 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?
Mapping out your trip in and around Winchester is easy with these transportation options. Fly into Lexington, KY (LEX-Blue Grass), which is located 23 mi (37.1 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia