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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 5 B&B in Winchester with updated reviews, rates, and availability.

Artistic Lodging Queen suite
1 bedroom, WiFi, bed sheets

Artistic Lodging Queen suite

9.6 out of 10, Exceptional, (37)
"What an enjoyable experience! The home is beautiful and I love all the art!!!!"
The price is AED 275
AED 466 total
includes taxes & fees
27 Apr - 28 Apr
Artistic Lodging Queen suite
Lyndon House B&B
Interior detail

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 804
AED 999 total
includes taxes & fees
5 May - 6 May
Lyndon House B&B
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 price is AED 617
AED 680 total
includes taxes & fees
6 May - 7 May
The Guesthouse at Rosecrest Farm
Artistic Lodging King Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

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
Suite, 1 King Bed (Dream Suite) | Free cribs/infant beds, free wired internet

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
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1532)
"Wonderful area"
The price is AED 426
AED 470 total
includes taxes & fees
29 Apr - 30 Apr
Natural Bridge State Resort Park
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Outdoor spa tub

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (143)
"Easy check in and stay, family loved it"
The price is AED 437
AED 898 total
includes taxes & fees
7 May - 8 May
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Tranquil Getaway in the Woods ~ Sunset Ridge
Terrace/patio

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (53)
"The perfect cabin for a weekend get away. Clean, cute, and cozy. "
The price is AED 386
AED 547 total
includes taxes & fees
27 Apr - 28 Apr
Tranquil Getaway in the Woods ~ Sunset Ridge
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. Artistic Lodging Queen suite: 15.8 mi (25.4 km) from the downtown core. The Guesthouse at Rosecrest Farm: 3 rooms. Situated 12.4 mi (20 km) from the heart of Winchester. Enjoy the free full breakfast and unique décor. Artistic Lodging King Suite: 15.8 mi (25.4 km) from the heart of downtown.
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 Cassell Creek 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.