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Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

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
Exterior

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, (1527)
"We stayed in a cottage. The cottage needs a lot of repairs. We had to climb 36 stairs in rainy conditions to reach our cabin. The complimentary breakfast was nice. The staff were all friendly and helpful. The walk to the restaurant from the cottages was outstanding and fun. Despite the state of disrepair to our cabin, we would still recommend this location as a must-do family adventure and destination."
The price is CA $160
CA $177 total
includes taxes & fees
Apr 29 - Apr 30
Natural Bridge State Resort Park
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Outdoor spa tub

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (142)
"Was an amazing stay"
The price is CA $165
CA $335 total
includes taxes & fees
Apr 20 - Apr 21
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Tranquil Getaway in the Woods ~ Sunset Ridge
Terrace/patio

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (53)
"The perfect cabin for a weekend get away. Clean, cute, and cozy. "
The price is CA $145
CA $206 total
includes taxes & fees
Apr 21 - Apr 22
Tranquil Getaway in the Woods ~ Sunset Ridge
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.