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Compare 9 B&B in Winchester with updated reviews, rates, and availability.

Blue Heron B&B and Retreat Center
Front of property
Blue Heron B&B and Retreat Center
3.5 star property
9.4 out of 10, Exceptional, (28)
"Very lovely place to stay"
Blue Heron B&B and Retreat Center
Artistic Lodging King Suite
Bathroom
Artistic Lodging King Suite
9.2 out of 10, Wonderful, (62)
"My husband and I drove to Paris, KY for a long weekend to celebrate our anniversary. Artistic lodging is located just a block off the Main Street. The spacious room is on the second floor of this beautifully restored home with original beautiful floors, a nice kitchen on the first floor and beautiful artwork adorning the walls. The full bathroom adjoining the room is also spacious and included everything necessary for our stay. The bedroom is nicely furnished and very comfortable! Everything was...
Artistic Lodging King Suite
Lyndon House B&B
Front of property
Lyndon House B&B
3.0 star property
9.6 out of 10, Exceptional, (103)
"Such a beautiful building and the furnishings inside are so original to the era the house was built."
The price is AED 732
AED 875 total
includes taxes & fees
10 Jun - 11 Jun
Lyndon House B&B
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Artistic Lodging Queen suite
Interior
Artistic Lodging Queen suite
9.4 out of 10, Exceptional, (34)
"Very neat and clean, close to everything we wanted!"
Artistic Lodging Queen suite
Stylish Kentucky hospitality
The front of the house on a beautiful Summer day.
Stylish Kentucky hospitality
10.0 out of 10, Exceptional, (11)
"Our stay was wonderful. Anton and his staff provided excellent service and the facility is just as advertised; excellent. Our family dinner with wine pairings was great, Anton worked with us in developing a menu that was perfect for our family. Location is perfect, short walk into downtown and easy access from the interstate."
The price is AED 5,877
AED 8,156 total
includes taxes & fees
7 Jul - 8 Jul
Stylish Kentucky hospitality
The Guesthouse at Rosecrest Farm
Exterior
The Guesthouse at Rosecrest Farm
3.0 star property
9.8 out of 10, Exceptional, (13)
"Really enjoyed the tour of the horse farm. Great hosts and nice accommodations in a beautiful setting."
The Guesthouse at Rosecrest Farm
The Bennett House Bed & Breakfast
Property grounds
The Bennett House Bed & Breakfast
3.0 star property
8.8 out of 10, Excellent, (90)
"Our reservations were canceled due to the corona virus. Unfortunately, we were not informed of this by expedia. Owners were very gracious and offered us a room, minus breakfast. We were delighted with the guest house and hope to return and enjoy their highly praised breakfast when life returns to normal!"
The Bennett House Bed & Breakfast
Chateau Annette
Exterior
Chateau Annette
3.5 star property
9.8 out of 10, Exceptional, (11)
"Ben and Annette are delightful hosts who provide a charming visit with world-class American breakfast. Chateau’s located near Keeneland Racecourse. Highly recommend!"
Chateau Annette
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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.

Other property types in Winchester

Natural Bridge State Resort Park
Hiking
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1325)
"Beautiful views. Property could use a finish refresh but the beds are comfortable and staff are friendly. Would stay again."
The price is AED 481
AED 530 total
includes taxes & fees
9 Jun - 10 Jun
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (242)
"The cabin was amazing. Nice and peaceful location. The cabin had everything that we needed. The jacuzzi was nice and relaxing, My wife enjoyed it very much! We are planning to get one at home shortly. The location of the property was a little puzzling at first. When we started to venture of and visit locations. The placement of the property made perfect sense! You’re literally right in the middle of everything that you will want to see! Everything interesting is just a few miles away! My wife...
The price is AED 393
AED 781 total
includes taxes & fees
12 Jun - 13 Jun
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Property grounds
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (99)
"This was a great property that was exactly the way it was described in VRBO. Would definitely stay here again!"
The price is AED 474
AED 826 total
includes taxes & fees
9 Jun - 10 Jun
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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.

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, Lykins Park and Community Park 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.
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, Lykins Park and Community Park are some notable spots. You might put Bluegrass Heritage Museum and Southwind 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.

Recent reviews of Winchester hotels
Expedia verified reviews

Natural Bridge State Resort Park

Natural Bridge State Resort Park

5/5 Excellent
"Enjoyed our stay!"
A verified traveler from PAOLI stayed at Natural Bridge State Resort Park
Posted 2 days ago
Natural Bridge State Resort Park