Photo by Hyelsinta

Search Winchester Villa Rentals

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Browse Select Winchester Villas

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

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

10.0 out of 10, Exceptional, (35)
"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
Miscellaneous

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
Sign in
Sign up, it's free

Other property types in Winchester

Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1499)
"You can walk out the door and do great hikes."
The price is CA $160
CA $177 total
includes taxes & fees
Mar 9 - Mar 10
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
TV, books

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

9.8 out of 10, Exceptional, (281)
"The cabin is lovely! Everything was clean and all the extras provided made this a comfortable stay. "
The price is CA $134
CA $288 total
includes taxes & fees
Mar 5 - Mar 6
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Exterior

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (62)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is CA $149
CA $312 total
includes taxes & fees
Mar 5 - Mar 6
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
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 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.
What is there to do near my villa in Winchester?
If you want to see the sights of Winchester, don’t miss Southwind Golf Course. It’s a favorite among locals and visitors alike.