Winchester Holidays
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Top hotels in Winchester
Best Western Winchester Hotel
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on 14 Dec, 2025
Hampton Inn Winchester
Overall the hotel was good - very friendly staff, safe area, clean and presentable. I was quite surprised and astonished by the $75 pet fee - it is outrageous for adding a dog to add $75 to a $150 room. This also was not clearly presented during the booking process.
Reviewed on 4 Jan, 2026
Baymont by Wyndham Winchester
Everything was perfect.
Reviewed on 27 Dec, 2025
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
Experience Rebecca Ruth Chocolate Tour & Museum!
Unique Horse Farm Tours with Insider Access to Private Farms
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* 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.
