Winchester Holidays
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Top hotels in Winchester
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is €198 per night from 26 May to 27 May
€198
26 May - 27 May
includes taxes & fees
9.6/10 Exceptional! (1,280 reviews)
Hôtel is beautiful but the staff are very cold
Reviewed on 13 May 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is €103 per night from 17 May to 18 May
€103
17 May - 18 May
includes taxes & fees
9.4/10 Exceptional! (2,190 reviews)
Doors close very loudly.
Reviewed on 13 May 2026
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is €145 per night from 21 May to 22 May
€145
21 May - 22 May
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Room was clean and comfy and had everything you needed.
Reviewed on 11 May 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
Kentucky Horse Park
Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
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.
What to do in Winchester
Experience Rebecca Ruth Chocolate Tour & Museum!
€9
per adult
80% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
€50
per adult
90% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum
€9
per adult
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