Winchester Vacations
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- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
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Find the Best Winchester Vacation Packages
Winchester Hotel Deals
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is ₩152,753 per night from Feb 24 to Feb 25
₩152,753
₩168,394 total
Feb 24 - Feb 25
includes taxes & fees
9.2/10 Wonderful! (456 reviews)
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 Jan 4, 2026
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is ₩284,577 per night from Feb 22 to Feb 23
₩284,577
₩355,440 total
Feb 22 - Feb 23
includes taxes & fees
9.4/10 Exceptional! (1,164 reviews)
Friendly staff great room wonderful ambience lovely restaurant.. great valet all round an amazing stay..,Thanks Manchester
Reviewed on Feb 15, 2026
Hyatt Regency Lexington
401 W High St Lexington KY
The price is ₩207,910 per night from Mar 8 to Mar 9
₩207,910
₩241,320 total
Mar 8 - Mar 9
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
Room was great! Staff was awesome. Being able to go into Rupp without going outside, the best.
Reviewed on Feb 9, 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.
Discover the most popular places to visit in Winchester
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Kentucky State Capitol
After visiting Kentucky State Capitol, make a plan to see the other sights and activities in Frankfort. Attend a sporting event in the area, or seek out the hiking trails.
Kroger Field
Catch an event at Kroger Field, and enjoy other activities in Lexington such as horseback riding. Experience the area's acclaimed theater scene or attend a sporting event.
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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.
