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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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Stay near Winchester's top sights

Photo of Winchester Peddlers Mall
Winchester Peddlers Mall3 locals recommend
Photo of Kroger
Kroger3 locals recommend
Photo of Blue Isle Home-Style Restaurant and Bar
Blue Isle Home-Style Restaurant and Bar4 locals recommend
Photo of Engine House Pizza Pub
Engine House Pizza Pub9 locals recommend
Photo of The Daily Grind
The Daily Grind4 locals recommend
Photo of Legacy Grove Park
Legacy Grove Park4 locals recommend

Other great vacation rentals in Winchester

Rental unit in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
$85 per night
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Loft in Winchester
Artist’s Loft 2Bdr Winchester, near Lexington KY
$167 per night
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Guesthouse in Winchester
Escape and unwind in the country
$75 per night
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Rental unit in Winchester
2nd Story Historic Downtown 2 BR w Modern Comforts
$100 per night
Farm stay in Winchester
The Winchester Retreat
$100 per night
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Home in Winchester
Renovated Farmhouse on 75 Acres
$149 per night
Home in Mount Sterling
THE DOLLY - Cozy, Bright Home in Historic Downtown
$74 per night
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Home in Winchester
Park View Cottage-3 Bedroom!
$171 per night
Guesthouse in Lexington
'Edith' Carriage House Getaway - I-75/Hamburg!
$55 per night
Rental unit in Lexington
Charming Modern Apartment w/ High-end Amenities 💙
$73 per night
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Home in Lexington
Cozy 2BR | Garage | Fire Pit | By Interstate +WiFi
$70 per night
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Farm stay in Winchester
Cozy Cottage Franklin Ridge Farms
$115 per night
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