Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Winchester
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is 4.411.359 ₫ per night from 22 Mar to 23 Mar
4.411.359 ₫
5.573.935 ₫ total
22 Mar - 23 Mar
includes taxes & fees
9.6/10 Exceptional! (1,181 reviews)
Remarkable MCM hotel with unique taste throughout. Friendly staff. Cozy bar, restaurant and lounge.
Reviewed on 2 Mar 2026
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is 3.001.882 ₫ per night from 12 Mar to 13 Mar
3.001.882 ₫
3.484.284 ₫ total
12 Mar - 13 Mar
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Great staff!!
Reviewed on 2 Mar 2026
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is 3.931.631 ₫ per night from 31 Mar to 1 Apr
3.931.631 ₫
4.563.444 ₫ total
31 Mar - 1 Apr
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Of the 4 Hilton's I stay in regularly in KY and TN, this one has room for improvement. Building is very old and was the most luxurious of the downtown hotels. Unfortunately all that was lost during a bad renovation. Property is not a luxury hotel at all. Problems everywhere. Horrible wall paper pealing ...
Reviewed on 28 Feb 2026
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.
Lexington Opera House
You can get tickets for a performance at Lexington Opera House during your stay in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
