Winchester Vacations
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Find the Best Winchester Vacation Packages
Winchester Hotel Deals
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is ₩121,918 per night from Apr 28 to Apr 29
₩121,918
₩134,403 total
Apr 28 - Apr 29
includes taxes & fees
7.2/10 Good! (787 reviews)
It was a great experience
Reviewed on Apr 16, 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is ₩145,020 per night from May 3 to May 4
₩145,020
₩168,327 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (2,174 reviews)
We had a very nice stay. Our room was very clean and we had a great breakfast.
Reviewed on Apr 17, 2026
Spark by Hilton Lexington Hamburg
2381 Buena Vista Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is ₩121,166 per night from Apr 26 to Apr 27
₩121,166
₩140,640 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (434 reviews)
Room was clean, pool was nice and cool, staff was great
Reviewed on Apr 16, 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.
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.
