Winchester Holidays
Top hotels in Winchester
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
"Room was fine, time to get new mattresses. Only 2.lottle runes of body wash in room. Sheets were clean but not that really nice clean smell."
Reviewed on 5 Jun, 2026
The Manchester
"This property is as advertised, a cool historic older B&B that’s got lots of character and is centrally located. The breakfast is solid and the Inn Keeper is a really nice guy who personalizes the experience. Their outdoor patio is very nice."
Reviewed on 5 Jun, 2026
DoubleTree Suites by Hilton Hotel Lexington
"Clean and staff was very helpful."
Reviewed on 4 Jun, 2026
Popular places to visit
Keeneland Racing Course
Enjoy a trip to Keeneland Racing Course and popular activities such as horse riding in Lexington. You can attend a sporting event while in the area.
Rupp Arena
Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.
What to do in Winchester
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
