Winchester Vacation Packages
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Your Winchester Vacation
Take away the hard part of organizing your next epic adventure with a Winchester vacation package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
Winchester Hotel Deals
Hampton Inn Winchester
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
The Manchester was a great experience. Its location is ideal. Unfortunately my stay was brief, checked in late and slept until right before checkout. I can only speak to the comfort of the rooms, which was excellent, and the courteousness of staff, also excellent. The atmosphere and ambiance are ...
Reviewed on Feb 5, 2026
Hilton Lexington/Downtown
Nice quiet room. Staff were very helpful.
Reviewed on Jan 16, 2026
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.
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
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour
