Winchester Traveling Trail Tours

Plan a trip to see Winchester Traveling Trail

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
Price was $841, price is now $688 per person
$688
per person
Oct 2 - Oct 6
found 2 days ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
8.6/10 Excellent! (1,002 reviews)
The complimentary breakfast was delicious! I had a spinach, mushroom, and cheese omelette. It was so good! The rooms were very spacious and comfortable as well.

Reviewed on Aug 24, 2025

Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was $888, price is now $739 per person
$739
per person
Oct 2 - Oct 6
found 2 days ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
8.8/10 Excellent! (988 reviews)
Overall, the stay was okay. However, I had to go to the front desk several times about housekeeping. I requested daily housekeeping at check in but after about 4 days of no housekeeping had to go to the front desk to request that my trash and towels be changed. The sign in the bathroom says housekeeping every other day, so I was surprised that I went that long without housekeeping. Even when housekeeping did come, there were several times that the bed was not made.

Reviewed on Aug 24, 2025

The Manchester

The Manchester

4 out of 5
Distillery District
Price was $1,308, price is now $1,129 per person
$1,129
per person
Oct 2 - Oct 6
found 2 days ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
9.6/10 Exceptional! (954 reviews)
Epic hotel. True old school bourbon eloquence vibe. Everything was spectacular. The lobby, the room, the outdoor alley breakfast area, and the epic rooftop bar that overlooks the city.

Reviewed on Aug 23, 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

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
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
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
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 1,192 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.