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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

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, (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
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.
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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, (1488)
"This was our second time staying here. The staff at the hotel are very friendly and helpful. The rooms are clean and well maintained. Our only complaint about the room is that during the winter season they are cold. There are no heavy blankets or comforters provided. Only a thin bedspread. Also the breakfast is very sparse. Only waffles, toast, bagels, cold cereal and instant oatmeal. The coffee is really bad as well, very muddy"
The price is CA $124
CA $136 total
includes taxes & fees
Feb 1 - Feb 2
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, (277)
"Very good"
The price is CA $133
CA $279 total
includes taxes & fees
Feb 2 - Feb 3
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Terrace/patio

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Gorgeous Fall foliage @ a quaint cabin close to everything "
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
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.
What is there to do near my villa in Winchester?
The ultimate travel accessory is a well-planned itinerary. Bluegrass Heritage Museum is a good place to kick-start your exploration of Winchester.