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About Vacation Rentals in Berkshires

Berkshires is a blend of museums, historic sites, dance, and art. Besides a thriving cultural scene, Berkshires is an active vacationers dream destination with rivers, lakes and hills. The Berkshire Hills is an idyllic destination for guests of Massachusetts Vacation Homes, with dozens of unique townships and recreational areas offering the visitor a grand vacation. Wealthy families from New York and Boston built 'summer cottages' in the Berkshires more than a century ago. And many of the surviving mansions have become fine inns or museums. Some of them have had their grounds converted to outdoor venues for performing-arts groups. These mansions offer you the unique experience of the great past of Berkshires on your vacation.

When it comes to hiking and other outdoor activities, it is Berkshires that leads the way! The famed Appalachian Trail, the longest continuous mountain trail in the United States, extends through the Berkshires and draws hikers by the hordes. Go for a hike in the woods that takes you through mountain paths and discover new areas of the Berkshires – Hopkins Forest, Wahconah Falls, Olivia’s Overlook or Tyringham Cobble. Check the latest trail activities with Williamstown Rural Lands Foundation – be sure to ask about The Hopper or Sheep Hill.

The Ashuwillticook Rail Trail offers free family activities with biking being the most popular! You'll get 11 miles of paved trail running along Route 8 between Adams and Pittsfield. You will also get to see the engineers of nature at work in Berkshires! Yes, you can see beaver lodges made from tree branches and mud or join a canoe trip along the Housatonic River where nature brings her glory for you to enjoy.

Ioka Valley Farm, Hancock, offers seasonal activities from harvesting tree sap and making maple syrup to riding in a giant 'pumpkin.'  Winter is playtime in the area. Jiminy Peak, Hancock, is a family retreat in the Berkshires loaded with year-round activities. Winter brings exciting downhill skiing and snow tubing, while spring through fall explode with a range of wild and active fun: bungee-jumping, rock-climbing, the Alpine Slide, trout fishing, and mountain biking! You'll also enjoy a guided snowmobile ride to the top of Mount Greylock.