An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Winchester cabins

We found 5 cabins — enter your dates for availability

Explore Winchester cabin rentals

Image of Historic Log Cabin - Farm - Near RRG and Lex. Learn about organic farming

Historic Log Cabin - Farm - Near RRG and Lex. Learn about organic farming

Sleeps 7 · 4 bedrooms

Image of Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Premier Host

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Sleeps 14 · 2 bedrooms · 2 bathrooms

Image of 1800’s Historical Log Cabin near I-75 Interstate

Premier Host

1800’s Historical Log Cabin near I-75 Interstate

Sleeps 6 · 2 bedrooms · 2+ bathrooms

Image of Cabin in Kentucky Horse Country

Premier Host

Cabin in Kentucky Horse Country

Sleeps 2 · 1 bedroom · 1 bathroom

Image of New cabin near Red River Gorge, fire pit, walk to hiking

New cabin near Red River Gorge, fire pit, walk to hiking

Sleeps 6 · 2 bedrooms · 1+ bathroom

Image of Cozy 2-bedroom rustic cabin in Red River Gorge area,Hot Tub, Pilots Knob Hiking

Premier Host

Cozy 2-bedroom rustic cabin in Red River Gorge area,Hot Tub, Pilots Knob Hiking

Sleeps 4 · 2 bedrooms · 1+ bathroom

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