
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 ¥11,763 per night from Aug 10 to Aug 11
¥11,763
¥12,968 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (731 reviews)
"The staff was exceptionally friendly and the hotel, room and pool were very clean. But, the bed that we had was hard and pillows were lumpy and very uncomfortable."
Reviewed on Jul 28, 2025

Value Stay
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is ¥8,697 per night from Aug 4 to Aug 5
¥8,697
¥9,587 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very Good! (84 reviews)
"Nice clean place"
Reviewed on Jul 13, 2025

GLō Best Western Lexington
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is ¥13,779 per night from Aug 24 to Aug 25
¥13,779
¥15,993 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (2,250 reviews)
"Great hotel!"
Reviewed on Jul 30, 2025
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

Kentucky Horse Park
4.5/5(328 reviews)
Explore Kentucky Horse Park, a favorite green space in Lexington, and also enjoy the area's horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
4.5/5(384 reviews)
Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Fayette Mall
4.5/5(321 reviews)
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
What to do in Winchester

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
¥4,396
per traveler

Experience Rebecca Ruth Chocolate Tour & Museum!
¥1,477
per adult

Lexington: Downtown Walking Food & History Tour
¥14,512
per adult
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.