Winchester Vacations
Book a Hotel + Flight or Car together to unlock savings
- 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
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is NT$6,318 per night from Mar 29 to Mar 30
NT$6,318
NT$7,878 total
Mar 29 - Mar 30
includes taxes & fees
9.6/10 Exceptional! (1,174 reviews)
Very nice clean room and staff was very friendly and accommodating
Reviewed on 2026/2/26
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is NT$3,626 per night from Mar 12 to Mar 13
NT$3,626
NT$4,209 total
Mar 12 - Mar 13
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Everything was nice.
Reviewed on 2026/2/23
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is NT$4,752 per night from Mar 31 to Apr 1
NT$4,752
NT$5,515 total
Mar 31 - Apr 1
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Yes everything was good!
Reviewed on 2026/2/20
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.
Buffalo Trace Distillery
You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while 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.
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.
