Photo by Hyelsinta

Search B&B in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 8 B&B in Winchester with updated reviews, rates, and availability.

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 Queen suite

9.4 out of 10, Exceptional, (37)
"All good… would recommend this place to anyone. Comfortable, quiet place, convenient to downtown shops and restaurants."
The price is AED 275
AED 466 total
includes taxes & fees
31 Jan - 1 Feb
Artistic Lodging Queen suite

The Guesthouse at Rosecrest Farm

3.0 star property
10.0 out of 10, Exceptional, (15)
"Roosecrest farm is an enchanting experience. We loved staying with the horses, learning about the history of horse racing and enjoying the beauty of the scenery. It's a very peaceful and special place."
The Guesthouse at Rosecrest Farm

Lyndon House B&B

3.0 star property
9.6 out of 10, Exceptional, (108)
"Great bed and breakfast with super friendly and knowledgeable Innkeeper. Highly recommend "
The price is AED 915
AED 1,093 total
includes taxes & fees
27 Jan - 28 Jan
Lyndon House B&B

Artistic Lodging King Suite

9.2 out of 10, Wonderful, (70)
"Perfect from beginning to end! The Lion and Rose was beautiful inside and out! The hosts were so charming and helpful in recommending restaurants and activities! The room we stayed in was beautiful and luxurious!! We will be back next year!"
Artistic Lodging King Suite

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 3,890
AED 5,525 total
includes taxes & fees
27 Jan - 28 Jan
Stylish Kentucky hospitality

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

3.5 star property
10.0 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
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1487)
"This was our second time staying here. The staff at the hotel are very friendly and helpful. The rooms are clean and well maintained. Our only complaint about the room is that during the winter season they are cold. There are no heavy blankets or comforters provided. Only a thin bedspread. Also the breakfast is very sparse. Only waffles, toast, bagels, cold cereal and instant oatmeal. The coffee is really bad as well, very muddy"
The price is AED 316
AED 348 total
includes taxes & fees
24 Jan - 25 Jan
Natural Bridge State Resort Park

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.8 out of 10, Exceptional, (274)
"My husband and I enjoyed a relaxing getaway! We loved the house, the balcony, and hot tub."
The price is AED 340
AED 749 total
includes taxes & fees
29 Jan - 30 Jan
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

10.0 out of 10, Exceptional, (127)
"Clean and quaint. Good communication with the renter. "
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, 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?
Here are some well-liked B&Bs in the area: Blue Heron B&B and Retreat Center: 3 rooms. 10.4 mi (16.7 km) from the heart of Winchester. Enjoy the free full breakfast and soaking bathtubs. Lyndon House B&B: 7 rooms. 17.5 mi (28.2 km) from the downtown core. Enjoy the free cooked breakfast and outdoor tennis. Artistic Lodging Queen suite: Situated 15.8 mi (25.4 km) from the heart of Winchester. Artistic Lodging King Suite: 15.8 mi (25.4 km) from the heart of downtown. The Guesthouse at Rosecrest Farm: 3 rooms. Located 12.4 mi (20 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
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 Clark County Public Library 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.