Winchester, Kentucky, United States
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Weather in Winchester

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Vacation Rentals in Winchester

Looking for a vacation rental in Winchester? has 256 vacation rental homes available in Winchester. You'll find 1 studios, 172 1-bedroom, 34 2-bedroom and 49 rentals with 3 or more bedrooms ranging from $36 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Winchester is $204 while the average price of a weekly rental is $990. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Winchester home is $4455.

Wondering if you can bring your dog or cat along with you? There are 93 pet-friendly vacation rentals available in Winchester. In addition to accommodating pets, Winchester rentals offer a variety of amenities. In particular, 175 rentals have Internet and WiFi, 161 have TV and/or cable and 83 have a pool or hot tub.

Search properties from 7 vacation rental sites in Winchester where the top providers in that area are HomeAway, HRS Holidays, and There are 87 HomeAway rentals, 63 HRS Holidays short term rentals and 40 vacation rentals.