
Winchester Holidays from £1,221
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Your Winchester Holiday
Take away the hard part of organising your next epic adventure with a Winchester holiday 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 holiday is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
Top Winchester Flight + Hotel Deals

Hotel LEX, Trademark Collection by Wyndham
Reviewed on 18 Aug 2025

Home2 Suites by Hilton Lexington University / Medical Center
Reviewed on 19 Aug 2025

Candlewood Suites Lexington Medical District by IHG
Reviewed on 13 Aug 2025

Staybridge Suites Lexington S Medical Ctr Area by IHG
Reviewed on 24 Aug 2025

Homewood Suites by Hilton Lexington Fayette Mall
Reviewed on 19 Jul 2025
Winchester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Population | 18,400 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Bluegrass Heritage Museum, Community Park and Lykins Park |
Top hotels in Winchester

Quality Inn Lexington -Horse Park
Reviewed on 19 Aug 2025

DoubleTree Suites by Hilton Hotel Lexington
Reviewed on 22 Aug 2025

GuestHouse Lexington
Reviewed on 21 Aug 2025
Popular places to visit

Kentucky Horse Park
Explore Kentucky Horse Park, a favourite green space in Lexington, and also enjoy the area's horse riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
Take a campus tour or just explore the area 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.

Lexington Opera House
You can get tickets for a performance 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.
What to do in Winchester

Experience Rebecca Ruth Chocolate Tour & Museum!

Unique Horse Farm Tours with Insider Access to Private Farms

Lexington: Downtown Walking Food & History Tour
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.