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Search B&B in Winchester

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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
1 Jan - 2 January 2025
Blue Heron B&B and Retreat Center
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."
Artistic Lodging Queen suite
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
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 673
AED 804 total
includes taxes & fees
24 Dec - 25 Dec
Lyndon House B&B
Artistic Lodging King Suite
Bathroom

Artistic Lodging King Suite

9.2 out of 10, Wonderful, (69)
"A charming place in a great location. Clean, safe and quaint. The instructions getting keys etc were clear and simple. Only problem was hot water was barely hot enough to shower. Would recommend staying at this property."
The price is AED 331
AED 526 total
includes taxes & fees
24 Dec - 25 Dec
Artistic Lodging King Suite
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
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, (1475)
"EVERYTHING GREAT. ROOM DID NOT HAVE A MICROWAVE OVEN. "
The price is AED 316
AED 348 total
includes taxes & fees
5 Jan - 6 January 2025
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, (271)
"Quiet and peaceful retreat! Everything was as advertised and we had a great stay. "
The price is AED 340
AED 756 total
includes taxes & fees
8 Jan - 9 January 2025
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Nestled in the beautiful mountains of the Red River Gorge Area

Nestled in the beautiful mountains of the Red River Gorge Area

9.0 out of 10, Wonderful, (6)
"Cabin was great but absolutely 0 service or wifi. Offered a great getaway from reality "
The price is AED 636
AED 1,009 total
includes taxes & fees
31 Dec - 1 January 2025
Nestled in the beautiful mountains of the Red River Gorge Area
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, Community Park and Lykins 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: 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, Community Park and Lykins Park are some notable spots. You might put Southwind Golf Course and Bluegrass Heritage Museum 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.