Historic Shopping & Dining District of Winchester Tours and Activities

Popular places to visit

Image for Randolph County Courthouse

Randolph County Courthouse

After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester.

Randolph County Courthouse
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Winchester Golf Club

Enjoy a round of golf in Winchester at Winchester Golf Club.

Winchester Golf Club
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Winchester Speedway

Catch an event at Winchester Speedway during your trip to Winchester.

Winchester Speedway
Image for Levi Coffin House

Levi Coffin House

You can study the exhibits at Levi Coffin House, a museum with a storied past, during your trip to Fountain City. You can attend a sporting event while in the area.

Levi Coffin House
Image for IU Health Jay Hospital

IU Health Jay Hospital

If IU Health Jay Hospital is what brings you to town, hopefully you'll have a chance to explore more of Portland.

IU Health Jay Hospital
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Turkeyfoot Preserve

You can take time to visit Turkeyfoot Preserve during your travels to Greenville. While in this family-friendly area, you can enjoy the restaurants.

Turkeyfoot Preserve

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
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!
See all 140 properties in Historic Shopping & Dining District of Winchester
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.