Berkshires Vacation Rentals

Many people think of the small towns in Western Massachusetts as the cultural centers of the Berkshires, but these beautiful mountains also spill into New York. Berkshires, New York, vacation rentals have become popular for their views of the Hudson Valley and easy access from Interstate 87.

One of the best scenic loops can be found driving through the Hudson Valley on Highway 9 and then heading through the mountains on Taconic State Parkway or State Route 22. The change in scenery from broad river plains to rolling forests really showcases New York’s diverse topography and the fall foliage.

If you’re going in the winter, Catamount Ski Area is as close as any of the resorts in the Catskills, and the new quad chairlift will cut down on the lines.

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Chatham Center, NY
- J Castricato
  This charming, sunny, 1860's Farmhouse is beautifully furnished and has been completely updated with new appliances and all amenities. The first floor has a large living...Read more
Old Chatham, NY
- Old Chatham Guest House
  Lovely 2 bedroom Guest House located on 11 acre estate on a secluded country dirt road. Devoe Bird Sanctuary located across the road. Gardens, pick your own vegetables and herbs...Read more
Spencertown, NY
- Berkshires Hudson Valley Cottage
  This charming cottage on over 100 acres has glorious 50-mile views over the Hudson Valley. The surrounding area is beautiful and historic. Near the Massachusetts border, the...Read more