Photo by Hyelsinta

Search Villas in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 2 Villas in Winchester with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (34)
"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

Cozy A Frame house firepit, sauna, gym, fishing pond Station Camp Getaway Nurys

10.0 out of 10, Exceptional, (3)
"The place is great. Nice quiet area great scenery couldn't ask for better. House is very well supply and host were vary helpful. We will stay there again for sure."
Cozy A Frame house firepit, sauna, gym, fishing pond Station Camp Getaway Nurys
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1475)
"EVERYTHING GREAT. ROOM DID NOT HAVE A MICROWAVE OVEN. "
The price is AED 316
AED 348 total
includes taxes & fees
5 Jan - 6 January 2025
Natural Bridge State Resort Park

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.8 out of 10, Exceptional, (271)
"Quiet and peaceful retreat! Everything was as advertised and we had a great stay. "
The price is AED 340
AED 756 total
includes taxes & fees
8 Jan - 9 January 2025
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Nestled in the beautiful mountains of the Red River Gorge Area

9.0 out of 10, Wonderful, (6)
"Cabin was great but absolutely 0 service or wifi. Offered a great getaway from reality "
The price is AED 636
AED 1,009 total
includes taxes & fees
31 Dec - 1 January 2025
Nestled in the beautiful mountains of the Red River Gorge Area
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.

Frequently asked questions

Why book your villa in Winchester with Expedia?
Use Expedia to find your ideal villa in Winchester. Taking the kids on vacation? Take advantage of our filters to search for stays with amenities like a pool. If you’re on a budget, choose how much you’d like to spend and your preferred star rating. We’ll help you find the perfect place in tune with your style and taste.
How can I find cheap villas in Winchester?
With Expedia’s convenient filter tool, reserving cheap villas in Winchester is a cinch. To discover accommodations that will keep some cash in your pocket, refine your search results by budget, star rating and amenities.