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Winchester Vacation

Winchester overview

Winchester is a friendly locale known for its shops. You'll enjoy the ample beer and cheese options, along with outdoor areas for hiking and running. Plan a fun excursion to Commonwealth Stadium and Rupp Arena. Make some time to see popular sights such as University of Kentucky and Mary Todd Lincoln House. Winchester is a family-friendly destination while offering something for everyone.

Where to stay in Winchester

Whether you're planning to stay for a night or for the week, the area around Winchester has accommodations to fit every need. Search for hotels in Winchester with Hotels.com by checking our online map. Our maps display the areas and neighborhoods around all Winchester hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Winchester hotel deals are here with our lowest price guarantee.

How to get to Winchester

Fly in to Lexington, KY (LEX-Blue Grass), 25.1 mi (40.5 km) from downtown Winchester.

What to see around Winchester

Outdoor activities are on hand like football and running along with attractions such as:
  • • Lexington Ice Center
  • • Applebee s Park
  • • Whitaker Bank Ballpark
  • • Cliff Hagan Stadium
  • • Boone Tennis Stadium
It's notable for its hiking trails and favorite places for nature lovers that include:
  • • Lykins Park
  • • Community Park
  • • Kentucky River Museum
  • • Boone Station State Historic Site
  • • Raven Run Nature Sanctuary
Below are some favorite shopping areas to find that perfect souvenir—or simply browse:
  • • Richmond Centre Mall
  • • Victorian Square Mall
  • • The Mall At Lexington Green
  • • Fayette Mall
Some popular places in the area include:
  • • Commonwealth Stadium
  • • University of Kentucky
  • • Mary Todd Lincoln House
  • • Rupp Arena

When to visit Winchester

Wondering when's the best time to visit? Here are seasonal norms to help you plan your trip:

Seasonal temperature averages
  • January-March: 61°F day, 21°F night
  • April-June: 85°F day, 35°F night
  • July-September: 86°F day, 47°F night
  • October-December: 73°F day, 21°F night
Seasonal rainfall averages
  • January-March: 10.98 inches
  • April-June: 12.64 inches
  • July-September: 11.46 inches
  • October-December: 10.67 inches