Windsor house rentals
We found 126 house rentals — enter your dates for availability
Explore Windsor house rentals
Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!
Sleeps 10 · 1 bedroom · 1 bathroom
Massachusetts Vacation Rental w/ Deck & Grill
Sleeps 8 · 4 bedrooms · 3 bathrooms
Remote and Relaxing Cabin in the Berkshires
Sleeps 8 · 3 bedrooms · 2 bathrooms
19th c. Barn in the Berkshires
Sleeps 9 · 3 bedrooms · 2 bathrooms
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Sleeps 6 · 3 bedrooms · 2 bathrooms
Berkshire Lake access
Sleeps 6 · 4 bedrooms · 2 bathrooms
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