Winchester Traveling Trail Tours

Plan a trip to see Winchester Traveling Trail

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
per person
Aug 18 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Lexington (LEX)
8.6/10 Excellent! (1,008 reviews)
Top tier hotel to stay in. 10/10 would recommend, and I most definitely will be staying again.

Reviewed on Jul 6, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Sep 12 - Sep 15
found 11 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Wonderful hotel that used to be an old bank. Amazing room and amenities. Would definitely stay again.

Reviewed on Jul 13, 2025

The Manchester

The Manchester

4 out of 5
Distillery District
per person
Aug 18 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Lexington (LEX)
9.6/10 Exceptional! (906 reviews)
Fantastic property! The best hotel I’ve stayed at this year. The room was clean. The decor was fantastic. Bed was comfy. Loved the rooftop bar. And the restaurant is in the distillery district so super close to great restaurants, shops and bourbon. We will go back!

Reviewed on Jul 10, 2025

Popular places to visit

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

Fort Boonesborough State Park

4.5/5(38 reviews)

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

3.5/5(2 reviews)

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

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
Baymont by Wyndham Winchester
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
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
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
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
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
Avid Hotel Lexington - Hamburg Area by IHG
Avid Hotel Lexington - Hamburg Area by IHG
2.5 out of 5
1810 Bryant Rd, Lexington, KY
Avid Hotel Lexington - Hamburg Area by IHG
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
See all 1,214 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.