
Winchester Vacations
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Find the Best Winchester Vacation Packages
Winchester Hotel Deals

Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is NT$2,452 per night from Nov 2 to Nov 3
NT$2,452
NT$2,704 total
Nov 2 - Nov 3
includes taxes & fees
8.4/10 Very Good! (978 reviews)
"Nice place. Very affordable and clean."
Reviewed on 2025/9/27

Spark by Hilton Lexington Hamburg
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NT$2,092 per night from Oct 28 to Oct 29
NT$2,092
NT$2,428 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (171 reviews)
"This was our second stay at a Spark. When possible we would select Spark on future trips"
Reviewed on 2025/10/1

GuestHouse Lexington
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NT$2,285 per night from Oct 12 to Oct 13
NT$2,285
NT$2,653 total
Oct 12 - Oct 13
includes taxes & fees
8.2/10 Very Good! (1,392 reviews)
"Clean room and friendly staff"
Reviewed on 2025/10/1
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.
Discover the most popular places to visit in Winchester

University of Kentucky
4.5/5(384 reviews)
Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Fayette Mall
4.5/5(321 reviews)
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
![Kentucky State University was chartered in May 1886 as the State Normal School for Colored Persons, only the second state-supported institution of higher learning in Kentucky.[1] During the euphoria of Frankfort's 1886 centennial celebration, the city donated $1,500 towards the purchase of land for a new college on a bluff overlooking Frankfort.
The new school formally opened on October 11, 1887, with three teachers, 55 students, and John H. Jackson as president.[1] Recitation Hall](https://mediaim.expedia.com/destination/2/153e32620cffbd999fa3637cc30e197d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Kentucky State University
4/5(117 reviews)
Walk around the campus at Kentucky State University during your visit to Frankfort. You can seek out the hiking trails while in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.