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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 8 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"
The price is AED 771
AED 826 total
includes taxes & fees
21 Mar - 22 Mar
Blue Heron B&B and Retreat Center
The Guesthouse at Rosecrest Farm
Exterior

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
Artistic Lodging Queen suite
Interior

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
24 Feb - 25 Feb
Artistic Lodging Queen suite
Lyndon House B&B
Front of property

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 732
AED 875 total
includes taxes & fees
24 Feb - 25 Feb
Lyndon House B&B
Artistic Lodging King Suite
Bathroom

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
Chateau Annette
Exterior

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.
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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, (1496)
"Hiking trail was nice"
The price is AED 316
AED 348 total
includes taxes & fees
24 Feb - 25 Feb
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, (279)
"Loved the location but 4 wheel drive is highly recommend. Very steep driveway."
The price is AED 340
AED 729 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (62)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is AED 378
AED 800 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
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 College 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.
What are the best B&Bs in Winchester?
Here are some well-liked B&Bs in the area: Lyndon House B&B: 7 rooms. 17.5 mi (28.2 km) from the heart of Winchester. Enjoy the free cooked breakfast and outdoor tennis. Blue Heron B&B and Retreat Center: 3 rooms. 10.4 mi (16.7 km) from the downtown core. Enjoy the free full breakfast and soaking bathtubs. Artistic Lodging Queen suite: Situated 15.8 mi (25.4 km) from the heart of Winchester. The Guesthouse at Rosecrest Farm: 3 rooms. 12.4 mi (20 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. Artistic Lodging King Suite: Located 15.8 mi (25.4 km) from the core of Winchester.
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 College 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.