Windsor, MA, USA Vacation Rentals

Discover popular destinations in and around Windsor

Hudson Valley
2,631 vacation rentals
New England
34,353 vacation rentals
Vermont
4,460 vacation rentals
Lenox
664 vacation rentals
New York
15,799 vacation rentals
Stockbridge
699 vacation rentals
Jiminy Peak Mountain Resort
404 vacation rentals
Pittsfield
578 vacation rentals
Northampton
73 vacation rentals
The Berkshires
685 vacation rentals
Williamstown
202 vacation rentals
Hancock
427 vacation rentals
Otis
506 vacation rentals
Green Mountain National Forest
2,152 vacation rentals
Becket
505 vacation rentals
North Adams
279 vacation rentals
Western Gateway Heritage State Park
276 vacation rentals
Hinsdale
485 vacation rentals
Tanglewood Music Center
682 vacation rentals
Monterey
590 vacation rentals

Explore a selection of Windsor vacation rentals