Winchester Holidays

Photo by Nawa Aseen

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 S$115 per night from 2 Nov to 3 Nov
S$115
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (978 reviews)
"Nice place. Very affordable and clean."

Reviewed on 27 Sept, 2025

Best Western Winchester Hotel
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is S$103 per night from 28 Oct to 29 Oct
S$103
28 Oct - 29 Oct
includes taxes & fees
8.6/10 Excellent! (165 reviews)
"We enjoyed our stay with Spark. Thank you."

Reviewed on 26 Sept, 2025

Spark by Hilton Lexington Hamburg
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is S$113 per night from 12 Oct to 13 Oct
S$113
12 Oct - 13 Oct
includes taxes & fees
8.2/10 Very Good! (1,386 reviews)
"Pleasantly surprised! A very nice, reasonably priced room and a pretty good breakfast."

Reviewed on 27 Sept, 2025

GuestHouse Lexington
See all 1,155 properties in Winchester
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

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.

Keeneland Racing Course

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.

Rupp Arena

What to do in Winchester

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

S$54
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

S$63
per adult
88% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Makers Mark, Four Roses or Woodford Reserve or Bulleit or Others

Groups: Makers Mark OR Buffalo Trace OR Woodford or Others

S$231
per adult
Groups: Makers Mark OR Buffalo Trace OR Woodford or Others
See all activities in Winchester

* 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.