Winchester Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Nawa Aseen
- Plan, book, travel with confidence
- Better togetherSave up to NT$5,067 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Winchester Vacation Packages
Winchester Hotel Deals
Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
The price is NT$2,284 per night from Jan 18 to Jan 19
NT$2,284
NT$2,518 total
Jan 18 - Jan 19
includes taxes & fees
8.4/10 Very Good! (999 reviews)
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on 2025/12/14
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is NT$3,980 per night from Feb 8 to Feb 9
NT$3,980
NT$4,388 total
Feb 8 - Feb 9
includes taxes & fees
9.2/10 Wonderful! (455 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 2026/1/4
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is NT$2,390 per night from Jan 18 to Jan 19
NT$2,390
NT$2,635 total
Jan 18 - Jan 19
includes taxes & fees
7/10 Good! (773 reviews)
Great stay and the bed was extremely comfortable
Reviewed on 2026/1/11
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
University of Kentucky
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
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.
Lexington Opera House
You can enjoy a show at Lexington Opera House during your stay in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
