Winchester Traveling Trail Tours

Plan a trip to see Winchester Traveling Trail

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

2.5 out of 5
Price was $286, price is now $246 per person
$246
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Miami (MIA) to Lexington (LEX)
8/10 Very Good! (1,004 reviews)
the room was a normal room but refrigerator didnt work. and the heat was a little irratic.. it was clean and comfortable not to bad

Reviewed on Dec 5, 2025

Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $353, price is now $303 per person
$303
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Miami (MIA) to Lexington (LEX)
8.2/10 Very Good! (1,040 reviews)
Very friendly staff and clean. Dated hotel but very excited to see the new updates and renovations that are beginning!

Reviewed on Dec 5, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $415, price is now $359 per person
$359
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Room was huge. Bed was comfortable. Great stay. We will be back.

Reviewed on Nov 30, 2025

Popular places to visit

Recreation of the fort Daniel Boone settled. Informative and friendly docents.

Fort Boonesborough State Park

Find out about the history of Richmond when you spend time at Fort Boonesborough State Park. While in this family-friendly area, you can savor the top-notch restaurants.

Fort Boonesborough State Park

Wiseman Park

Explore the great outdoors at Wiseman Park, a lovely green space in Winchester. You can enjoy the restaurants while in the area.

Wiseman Park

GRCHS Baseball Field

Explore the great outdoors at GRCHS Baseball Field, a lovely green space in Winchester. You can enjoy the restaurants while in the area.

GRCHS Baseball Field

Clark County Public Library

After visiting Clark County Public Library, make a plan to see the other sights and activities in Winchester. You can enjoy the restaurants while in the area.

Clark County Public Library

College Park

Explore the great outdoors at College Park, a lovely green space in Winchester. You can enjoy the restaurants while in the area.

College Park

Clark Regional Medical Center

Though Clark Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

Clark Regional Medical Center

Best Lodging Options Near Winchester Traveling Trail

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
Best Western Winchester Hotel
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
GuestHouse Lexington
Hyatt Place Lexington

Hyatt Place Lexington

3 out of 5
2001 Bryant Rd Lexington KY
Hyatt Place Lexington
Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

3 out of 5
1750 PLEASANT RIDGE DR Lexington KY
Home2 Suites by Hilton Lexington Hamburg
Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg

2 out of 5
5575 Athens Boonesboro Rd Lexington KY
Days Inn Lexington SE/Hamburg
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
DoubleTree Suites by Hilton Hotel Lexington
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

3 out of 5
1976 Justice Dr Lexington KY
Holiday Inn Lexington - Hamburg by IHG
Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

3 out of 5
5532 Athens Boonesboro Rd Lexington KY
Hotel LEX, Trademark Collection by Wyndham
See all 1,258 properties in Winchester Traveling Trail
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.