Winchester Holidays

Top hotels in Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is S$113 per night from 26 Apr to 27 Apr
S$113
26 Apr - 27 Apr
includes taxes & fees
7.2/10 Good! (787 reviews)
It was a great experience

Reviewed on 16 Apr, 2026

Baymont by Wyndham Winchester
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$108 per night from 10 May to 11 May
S$108
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (440 reviews)
My biggest issue is "queen" size linens on a king bed!

Reviewed on 20 Apr, 2026

Spark by Hilton Lexington Hamburg
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is S$144 per night from 3 May to 4 May
S$144
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (2,185 reviews)
Excellent place to stay. Close to everything. Very clean. Safe area. Good value.

Reviewed on 20 Apr, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
See all 1,197 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

Horse barn in Kentucky

Keeneland Racing Course

4.5/5(3 reviews)

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
Aerial photograph of the Lexington, Kentucky skyline at night with the city alite.

Rupp Arena

4/5(1 review)

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$58
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
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
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

S$13
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
See all activities in Winchester

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