Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Home in Winchester

Bluegrass Bungalow 3 Bedroom Home

Welcome to Bluegrass Bungalow, a beautifully quaint home located in charming downtown Winchester, where you can relax with the hometown atmosphere. This home is a home away from home with all the amenities including washer/dryer, master with queen bed and 2nd bedroom with full and an office/bedroom for a work space. A short drive to downtown Lexington or you can relax with a hike at Red River Gorge. You are in close proximity to the best distilleries of the famous Kentucky Bourbon Trail.

$106 per night

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Loft in Winchester

Stylish Loft Historic Downtown 2Bdrm Winchester KY

New York style loft meets historic renovation—Central Kentucky. Meet charming Winchester. Under hr. to Keeneland race track, Kentucky Horse Park, & the spectacular Red River Gorge/Natural Bridge. Lexington 30 min. Paris, Georgetown, Richmond & Berea close too. Many local, small businesses-restaurants, brewery, distillery, shops, antiques, flea markets, & historical sites! Unit is on the second floor—may not be right for all abilities. Public, street parking. See our lovely town renovation.

$167 per night

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Guesthouse in Winchester

Carriage House Gardenside

Privacy and Convenience are yours when you stay at the NEW Carriage House Gardenside. Located in historic Winchester, Carriage House Gardenside offers easy access to Lexington, the Kentucky Horse Park, Keeneland Race Course, the Bourbon Trail and Red River Gorge. Situated across from College Park and steps away from Winchester's public gym (indoor swimming pool and fitness center). Space features a king sized bed, large TV, coffee bar, devoted work space and full bath.

$70 per night

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