Historic Shopping & Dining District of Winchester Tours and Activities



Popular places to visit


Top Historic Shopping & Dining District of Winchester Hotel & Accommodation Deals

Randolph Inn and Suites
Randolph Inn and Suites
2.5 out of 5
890 E Washington, Winchester, IN
Randolph Inn and Suites
Quaint Economy Retreat w/ Patio & Spacious Yard!
Quaint Economy Retreat w/ Patio & Spacious Yard!
Economy
Quaint Economy Retreat w/ Patio & Spacious Yard!
Quaint Economy Retreat w/ Patio & Spacious Yard!
Quaint Economy Retreat w/ Patio & Spacious Yard!
3 out of 5
Economy
Quaint Economy Retreat w/ Patio & Spacious Yard!
Holiday Inn Express & Suites Portland, an IHG Hotel
Holiday Inn Express & Suites Portland, an IHG Hotel
2.5 out of 5
100 Holiday Dr, Portland, IN
Holiday Inn Express & Suites Portland, an IHG Hotel
Red Roof Inn Richmond, IN
Red Roof Inn Richmond, IN
2 out of 5
2525 Chester Blvd, Richmond, IN
Red Roof Inn Richmond, IN
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Muncie
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Baymont by Wyndham Muncie Near Ball State University
Baymont by Wyndham Muncie Near Ball State University
2.5 out of 5
3400 North Chadam Lane, Muncie, IN
Baymont by Wyndham Muncie Near Ball State University
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Richmond
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
3 out of 5
Richmond
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.