A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester guest houses

We found 20 guest houses — enter your dates for availability

Explore Winchester guest house rentals

Image of Peaceful Secret Gardens Tiny Home - A space to relax and get away from it all.

Peaceful Secret Gardens Tiny Home - A space to relax and get away from it all.

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Delightful and Serene Hundred Year Old Sweet Space Among the Gardens

Delightful and Serene Hundred Year Old Sweet Space Among the Gardens

Sleeps 2 · 1 bedroom · 1 bathroom

Image of River View East - Full Bed

River View East - Full Bed

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Room In Central Historic Downtown - 1820 Suite

Premier Host

Room In Central Historic Downtown - 1820 Suite

Sleeps 6 · 1 bedroom · 1 bathroom

Image of Room In Central Historic Downtown -River View West

Room In Central Historic Downtown -River View West

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Riverfront Oasis with Mountain Views, close to town

Riverfront Oasis with Mountain Views, close to town

Sleeps 5 · 2 bedrooms · 1 bathroom

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Enjoy full kitchens, laundry, pools, gardens and more
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