Winchester Hotels

Search for hotels in Winchester

Save up to 40%!

Get instant savings with Secret Prices

  • Pay now or later on most rooms
  • Free cancellation on most rooms
  • Price Guarantee

Where to stay in Winchester

Winchester overview

Whatever your interests are, Winchester has something for you. Visitors to Winchester can take time to see places like Randolph County Courthouse and Winchester Golf Club. You may want to expand your exploration to the surrounding area to see Winchester Speedway and other sights.

Where to stay in Winchester

Whether you plan to stay for a night or a week, Winchester has the right accommodation for you. You can shop as many as 19 deals in Winchester for rooms on Hotels.com. Our room prices start at 48 USD per night and below are the number of hotels by star rating in Winchester as well as in the surrounding area:
  • • 17 3-star hotels from 84 USD per night
  • • 13 2-star hotels from 49 USD per night

How to get to Winchester

Fly in to Indianapolis, IN (IND-Indianapolis Intl.), 77.9 mi (125.3 km) from downtown Winchester.

What to see around Winchester

Recommended sights include:
  • • Randolph County Courthouse
  • • Winchester Golf Club

When to visit Winchester

Do you want to know the ideal time of year to visit? Here's a list of the seasonal weather norms to help with trip planning:

Seasonal temperature averages
  • • January-March: 57°F day, 19°F night
  • • April-June: 85°F day, 35°F night
  • • July-September: 85°F day, 47°F night
  • • October-December: 71°F day, 20°F night
Seasonal rainfall averages
  • • January-March: 8.27 inches
  • • April-June: 12.83 inches
  • • July-September: 10.08 inches
  • • October-December: 9.53 inches