
Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Nawa Aseen
Top hotels in Winchester

Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
The price is 1.904.608 ₫ per night from 4 Dec to 5 Dec
1.904.608 ₫
2.099.640 ₫ total
4 Dec - 5 Dec
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful.
Reviewed on 25 Nov 2025

The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is 5.317.557 ₫ per night from 14 Dec to 15 Dec
5.317.557 ₫
6.631.104 ₫ total
14 Dec - 15 Dec
includes taxes & fees
9.4/10 Exceptional! (1,058 reviews)
The staff was phenomenal, my bride and I wanted for nothing.
Reviewed on 26 Nov 2025

GuestHouse Lexington
2261 Elkhorn Road Lexington KY
Fully refundableReserve now, pay when you stay
The price is 1.550.262 ₫ per night from 7 Dec to 8 Dec
1.550.262 ₫
1.799.390 ₫ total
7 Dec - 8 Dec
includes taxes & fees
8.2/10 Very Good! (1,476 reviews)
a clean hotel and everything’s around, i would stay here again!
Reviewed on 26 Nov 2025
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.
Popular places to visit

Fayette Mall
You can do some window-shopping at Fayette Mall during your trip to Lexington. Discover the area's acclaimed theatre scene or seek out its horse riding.

The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Eastern Kentucky University
Enjoy the student vibe when you visit Eastern Kentucky University during your travels in Richmond. While in this family-friendly area, you can savour the top-notch restaurants.
