Winchester Traveling Trail Tours and Activities

Plan a trip to see Winchester Traveling Trail

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was CA $1,015, price is now CA $918 per person
CA $918
per person
Oct 31 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (988 reviews)
Closeness to shopping and eateries

Reviewed on Aug. 19, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,149, price is now CA $973 per person
CA $973
per person
Oct 31 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Beautiful historic building. Big rooms, views. Fantastic shower and the robes are luxurious touch. Wonderful gallery. Extremely friendly staff.Stay here often.Live it!

Reviewed on Aug. 9, 2025

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was CA $1,381, price is now CA $1,248 per person
CA $1,248
per person
Oct 31 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
9.4/10 Exceptional! (820 reviews)
Like: The neighborhood and close dining. Breakfast was nice. Staff were awesome! Thank you. A little bit let down by the "spa shower".

Reviewed on Jul. 29, 2025

Popular places to visit

Fort Boonesborough State Park

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

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
Hyatt Place Lexington

Hyatt Place Lexington

3 out of 5
2001 Bryant Rd, Lexington, KY
Hyatt Place Lexington
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
GuestHouse Lexington
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
Comfort Inn Lexington I-75

Comfort Inn Lexington I-75

2.5 out of 5
5531 Athens Boonesboro Road, Lexington, KY
Comfort Inn Lexington I-75
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Spark by Hilton Lexington Hamburg
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
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
See all 1,199 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.