Winchester Holidays

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Top hotels in Winchester

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
The price is 1.904.391 ₫ per night from 14 Dec to 15 Dec
1.904.391 ₫
2.099.401 ₫ total
14 Dec - 15 Dec
includes taxes & fees
8.4/10 Very Good! (999 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

Best Western Winchester Hotel
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is 3.285.884 ₫ per night from 3 Jan to 4 Jan
3.285.884 ₫
3.813.925 ₫ total
3 Jan - 4 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Everything was great but the heat was stuck on and the thermostat didn’t work

Reviewed on 30 Nov 2025

Hilton Lexington/Downtown
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Fully refundableReserve now, pay when you stay
The price is 1.783.126 ₫ per night from 15 Dec to 16 Dec
1.783.126 ₫
2.069.673 ₫ total
15 Dec - 16 Dec
includes taxes & fees
8.2/10 Very Good! (1,496 reviews)
It was good for an overnight stay, convenient to restaurants and good price.

Reviewed on 2 Dec 2025

GuestHouse Lexington
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.

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