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 houses

We found 19 houses — enter your dates for availability

Explore Winchester house rentals

Image of 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Premier Host

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Image of Charming 3-Bedroom House with Pool, WiFi, AC in Tranquil Winchester

Premier Host

Charming 3-Bedroom House with Pool, WiFi, AC in Tranquil Winchester

Sleeps 6 · 3 bedrooms · 2 bathrooms

Image of Farmhouse living within sight of Lexington - Horse Paddock available

Farmhouse living within sight of Lexington - Horse Paddock available

Sleeps 6 · 3 bedrooms · 3 bathrooms

Image of River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky

Sleeps 6 · 3 bedrooms · 3 bathrooms

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

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