Winchester Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is ￥16,153 per night from Feb 21 to Feb 22
￥16,153
￥17,808 total
Feb 21 - Feb 22
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 ￥28,084 per night from Feb 24 to Feb 25
￥28,084
￥35,256 total
Feb 24 - Feb 25
includes taxes & fees
9.4/10 Exceptional! (1,161 reviews)
Friendly and attentive staff. Great location, bar and onsite restaurant.
Reviewed on Feb 9, 2026
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
The price is ￥21,989 per night from Feb 22 to Feb 23
￥21,989
￥25,523 total
Feb 22 - Feb 23
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
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.
Kentucky Horse Park
Enjoy a trip to Kentucky Horse Park and popular activities like horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
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.
What to do in Winchester
Experience Rebecca Ruth Chocolate Tour & Museum!
￥1,548
per adult
80% of travellers recommend
Sound Bath Meditation in Lexington
￥3,870
per adult
100% of travellers recommend
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.
