Photo by Hyelsinta

Search Villas in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Villas in Winchester

12acre Villa right by Keeneland-Keene Creek Estate 10,000sqft
Property grounds

12acre Villa right by Keeneland-Keene Creek Estate 10,000sqft

10.0 out of 10, Exceptional, (40)
"Everything went perfectly, if we ever go back to Lexington I will like to stay here again."
12acre Villa right by Keeneland-Keene Creek Estate 10,000sqft
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your villa in Winchester with Expedia?
Use Expedia to find your dream villa in Winchester. Getting away with the kids? Take advantage of our filters to search for stays with amenities like WiFi and a pool. If you have a budget in mind, choose how much you want to spend and your preferred star rating. We'll help you find the perfect stay in tune with your taste and style.
How can I find cheap villas in Winchester?
With Expedia's user-friendly filter tool, booking cheap villas in Winchester has never been easier. To discover accommodations that won't break the bank, refine your search results by star rating, amenities and budget.