Windsor, MA, USA Vacation Rentals

Discover popular destinations in and around Windsor

The Berkshires
881 vacation rentals
Hudson Valley
3,706 vacation rentals
Lenox
353 vacation rentals
Great Barrington
489 vacation rentals
Vermont
4,464 vacation rentals
Stockbridge
445 vacation rentals
New York
16,129 vacation rentals
Pittsfield
354 vacation rentals
Lee
473 vacation rentals
North Adams
113 vacation rentals
Tanglewood Music Center
673 vacation rentals
West Stockbridge
437 vacation rentals
Jiminy Peak Mountain Resort
416 vacation rentals
Northampton
48 vacation rentals
Columbia County
260 vacation rentals
New England
35,094 vacation rentals
Becket
319 vacation rentals
Williamstown
151 vacation rentals
Monterey
446 vacation rentals
Norwich Lake
34 vacation rentals

Explore a selection of Windsor vacation rentals