Berkshires Vacation Rentals

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Downstairs Bathroom

3BR / 2BA - Sleeps 7 - Stockbridge Home

Beautifully remodeled quaint 1930s home overlooking 5 riverfront acres, with all modern amenities including...

$300 / nt

Great Barrington Massachusetts Vacation Rentals - Cottage

4BR / 2BA - Sleeps 8 - Great Barrington Cottage

Located directly on the shore of Lake Buel in Great Barrington just minutes away from Tanglewood, Jacobs...

$267 - $284 / nt


2BR / 1BA - Sleeps 6 - Lee Apartment

Entirely remodeled 19th Century Apartment at Main Street of the Lee , spacious rooms , modern kitchen...

$175 / nt

3 Reviews

5BR / 4.5BA - Sleeps 12 - Great Barrington Home

This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park- like, sunny acres located...

$358 - $500 / nt


Studio / 1BA - Sleeps 4 - Charlemont Apartment

BREAKING NEWS: Cavalier Cottage has received, for the 2nd consecutive year, two distinguished awards...

$115 - $135 / nt

1 Review
Richmond Massachusetts Vacation Rentals - Home

2BR / 2BA - Sleeps 6 - Richmond Home

Beautiful new home in Richmond MA. Must be seen to be appreciated. Central air & high end heating system...

1 Review
Adams Massachusetts Vacation Rentals - Apartment

2BR / 1BA - Sleeps 4 - Adams Apartment

The Rental Is Located Below Beautiful Mt. Greylock. It Sits On An Acre Private Lot With Only One Other...

13 Reviews

Visiting the Berkshire Mountain Region in Massachusetts

Families that love New England weather and the great outdoors will have a wonderful time in the Berkshires! Vacation rentals are the perfect option for those looking for a home away from home while on vacation. By choosing to rent a home made available by owner, you’re guaranteed a beautiful, spacious rental that’s much more comfortable than a hotel room. While staying in a Berkshire vacation rental, visitors will have a blast exploring the area’s fun activities and attractions. These rentals fill up fast, so book your spot online in advance to save on costs.
Families staying in Berkshire rentals should know that the best way to get around the region is by car. Rentals are available from many local companies. Public transportation is also available in the area.
Areas within the Berkshires
Visitors interested in checking out Berkshire vacation rentals should know about these great places to visit:
  • Williamstown, known as “The Village Beautiful,” is a picturesque area surrounded by hiking trails and mountains. It features the Hopkins Memorial Forest and the Taconic Trail State Park.
  • Stockbridge is a perfect example of small-town New England. It was represented on the cover of The New York Post by artist Norman Rockwell and featured in the James Taylor song "Sweet Baby James."
  • Otis is a great place to visit for a taste of the great outdoors. With more than 20 ponds and lakes, this is a great spot for fishing and relaxing.
  • Pittsfield, also known as the “hub” of the Berkshires, has much to offer locals and tourists. Lots of shopping, outdoor activities, and fun events are available.
Sightseeing in the Berkshires and Things to Do
While enjoying their vacation rentals, Berkshires visitors have many options to keep them occupied! From museums to outdoor adventures, this area has something for every member of the family.
  • Magic Wings Butterfly Conservatory & Gardens is fun for the whole family! This 8,000-square-foot conservatory houses more than 4,000 tropical and native butterflies year-round.
  • The Norman Rockwell Museum houses the world’s largest collection of his original art.
  • Uncle Don’s Barnyard at Ioka Valley Farm is a wonderful option for families with kids looking for some New England charm. It includes a playground, sandboxes, a hay tunnel, and tons of friendly animals.
  • Zip-lining and water sports are perfect for active families looking for a little adventure! For families visiting in the winter, skiing and snowboarding are great options.
Regional Foods and Dining in the Berkshires
The Berkshires has become known for its farm-to-table approach to food. The food culture in the Berkshires focuses on using the best local, organic, and seasonal ingredients. The Berkshires are home to many award-winning restaurants as well as a few interesting food trails. Foodies staying in local Berkshire rentals will enjoy the Beer & Cider Trail and the Cheese Trail.
Berkshires Weather and Climate
The climate of the Berkshires is typical New England weather: mild summers and snowy winters. August is the warmest month, with temperatures reaching 74 degrees. In January, the daily average is about 27 degrees. The average snowfall in Berkshire County, MA, is 70 inches per year.
When to Visit the Berkshires
Families hoping to book their Berkshire house rentals early should think about visiting during one of the region’s many local festivals. Here are a couple of the most popular events:
  • The Fall Folliage Festival & Parade (late September through early October) has been going strong for more than 55 years! It features seasonal produce, homemade goods, a 5K race, and a fun parade.
  • The Rock, Rattle, & Drum American Indian Pow Wow (August) is a fun festival with native dancing, music, arts and crafts, and much more.
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