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.
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.
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.
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.
December, Low crowds, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
0°
4°
ac_unit
January, Low crowds, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
7°
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February, Low crowds, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
13°
weather_cloudy
March, Low crowds, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
3°
18°
weather_sun
April, High crowds, average high temperature 18 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
23°
weather_sun
May, High crowds, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
13°
28°
weather_sun
June, Moderate crowds, average high temperature 28 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
29°
weather_sun
July, Moderate crowds, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
weather_sun
August, High crowds, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
26°
weather_sun
September, Moderate crowds, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
19°
weather_sun
October, High crowds, average high temperature 19 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
9°
12°
weather_partly_sunny
November, Moderate crowds, average high temperature 12 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
Monthly weather averages (˚C)
Top landmarks in Winchester
Winchester Traveling Trail
If you like spending time outside, why not spend the afternoon at Winchester Traveling Trail, a park located 16.6 mi (26.8 km) from the center of Lexington. Want to stretch your legs some more? Head to Wiseman Park and GRCHS Baseball Field, both nearby.
The center of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Clark Regional Medical Center, Lykins Park, and Cassell Creek Golf Course.
You might want to practice your swing at Cassell Creek Golf Course, a golf course located 4.1 mi (6.6 km) from central Winchester. If Cassell Creek Golf Course doesn't quite scratch your golfing itch, Southwind Golf Course is also nearby.
Lykins Park is 2 mi (3.3 km) from central Winchester, why not stop by during your stay. Want to stretch your legs some more? Head to The Holler and Community Park, both nearby.
If you like spending time outside, why not spend the afternoon at The Holler, a park located 18.2 mi (29.2 km) from the center of Lexington. Want to stretch your legs some more? Head to Lykins Park and Community Park, both nearby.
You might want to practice your swing at Southwind Golf Course, a golf course located 2.2 mi (3.5 km) from central Winchester. If Southwind Golf Course doesn't quite scratch your golfing itch, Cassell Creek Golf Course is also nearby.
Beneath the shadow of the Bluegrass Heritage Museum, Main Street reveals a parade of antique shops where yesterday's treasures await discovery. The Winchester Opera House stands as a cultural cornerstone in this small Kentucky town with big character. Escape to Daniel Boone National Forest, where hiking trails wind through Appalachian wilderness that would make the legendary frontiersman feel right at home. College Park offers a peaceful retreat when urban exploration tires the feet. Local eateries serve up authentic flavors that chain restaurants can't replicate. For golf enthusiasts, Southwind Golf Course presents challenging fairways with scenic vistas. The Clark County Courthouse anchors the historic downtown, its architecture telling stories of bygone eras without saying a word.
"My husband and I stayed here for the night and had a great stay. We had our French bulldog with us too. They even gave us some dog treats for her! We would definitely stay here again. The rooms were clean and the beds were comfortable. The staff we interacted with were all very helpful and friendly."
If you want the flexibility to change your plans to Winchester, most properties offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winchester if I want a vacation home instead of a traditional hotel?
Browse 6 vacation homes on our site.
What will the weather in Winchester be like during my visit?
July and August are typically the warmest months in Winchester when the average temp is 72°F. January and February are the coldest months when the average temperature is 38°F. April and July are the months with the most rain.
Why should I book my Winchester accommodation with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.