Winchester Guest Houses

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Guest Houses in Winchester

Luxury on Main / North

Richmond KY

$153 nightly

$168 total

Apr 26 - Apr 27

Total with taxes and fees

With a stay at this guesthouse in Richmond, you'll be a 4-minute walk from Richmond Area Arts Center and 7 minutes by foot from Eastern Kentucky University.

Pet friendly

Air conditioning

"The Guest House", Located on a 300 acre horse farm.

Lexington KY

Located in Lexington, this guesthouse is within a 15-minute drive of Keeneland Racing Course and Red Mile Racetrack.

Air conditioning

Parking available

College Park Bungalow

Winchester KY

With a stay at this guesthouse in Winchester, you'll be a 1-minute walk from College Park and 7 minutes by foot from GRCHS Baseball Field.

Pet friendly

Air conditioning

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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.