
Winchester Vacations from $264
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Your Winchester Vacation
History, cuisine, art and more … There's so much to experience with a Winchester vacation package. And with the ability to customize your city getaway, you know it'll be one that's tough to forget. Want to explore? Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your vacation to Winchester to suit your style of travel, whatever that may look like.
The Latest Winchester vacation packages


Fairfield Inn & Suites by Marriott Indianapolis Carmel
Reviewed on Jul 13, 2025

Omni Severin Hotel
Reviewed on Jul 18, 2025


Discover the most popular places to visit in Winchester
Winchester Speedway
Catch an event at Winchester Speedway during your trip to Winchester.
Winchester Golf Club
Enjoy a round of golf in Winchester at Winchester Golf Club.
Winchester Hotel Deals

Randolph Inn and Suites
Reviewed on Jun 25, 2025

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Reviewed on Jul 14, 2025

Days Inn by Wyndham Muncie -Ball State University
Reviewed on Jul 14, 2025
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 4,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana |