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

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

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

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

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
Perfect place to unwind, relax and enjoy nature

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
Hiking

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1496)
"Hiking trail was nice"
The price is AED 316
AED 348 total
includes taxes & fees
24 Feb - 25 Feb
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

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

9.8 out of 10, Exceptional, (279)
"Loved the location but 4 wheel drive is highly recommend. Very steep driveway."
The price is AED 340
AED 729 total
includes taxes & fees
24 Feb - 25 Feb
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!

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 AED 378
AED 800 total
includes taxes & fees
24 Feb - 25 Feb
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 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.