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Berkshires Apartments & Vacation Rentals - 4 Rentals Available

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4 Vacation rentals

1 / 18

Great Barrington Log cabin

  • 2
  • 5
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $250 / night

(10)

1 / 24

Lee House

  • 4
  • 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
“I had such a wonderful weekend at the schoolhouse with nine other moms. The space is well appointed with comfortable furniture, inspiring artwork, a well-stocked kitchen, and a fireplace. I was surprised by the amount of space downstairs--a beautiful...”
- Review left on 12/11/2016

$350

Excellent (10 reviews)

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from $350 / night

(2)

1 / 29

Charlemont Studio

  • -1
  • 4
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“Great place to recharge, very pet friendly. Loved the setting and the scones, baked fresh every morning...”
- Review left on 04/17/2015

$134

Excellent (2 reviews)

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from $134 / night

1 / 19

Sheffield House

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1500

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from $1500 / night

Your search has been expanded 28.2 miles to include more rentals

(2)

1 / 11

Wilmington House - 27.5 miles away

  • 3
  • 7
  • Min stay varies
  • Ask about children
  • Pet friendly
“I stayed here for the weekend with my husband and all 4 of our parents. It was a good size for 6 adults, enough couch and kitchen seating for everyone. The kitchen seemed well enough stocked, we only had one meal at the house. We were there to ski at...”
- Review left on 02/19/2016

$175

Very Good (2 reviews)

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from $175 / night

1 / 16

Nassau House - 28.2 miles away

  • 3
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

from $143 / night

About Berkshires

Families that love New England weather and the great outdoors will have a wonderful time in the Berkshires. Take in the scenic landscape of western Massachusetts or indulge in the freshest of foods during your stay. Choose from a variety of Berkshires vacation rentals as your home away from home, and enjoy the perfect New England getaway. 

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 Fahrenheit. In January, the daily average is about 27 degrees. The average snowfall in Berkshire County is 70 inches per year. Check the weather before your trip to the Berkshires so you can pack appropriately and always bring layers to stay warm. 

Transit

The Berkshires are an easy drive or bus ride from both Boston and New York. Having a car is the best way to get around the region, and rentals are available from many local companies. If you’re without a car, public transportation is also available in the area. The Berkshire Regional Transit Authority provides services for the 24 communities within the county and service is available daily for a nominal fare.

Things to do

Aside from enjoying their Berkshires vacation rentals, visitors have many options to stay occupied during a trip to this part of Massachusetts. With a mix of cultural attractions, historic sights and outdoor activities, this area has something for every member of the family. Some favorites include:

  • The Norman Rockwell Museum: It houses the world’s largest collection of Norman Rockwell’s original art, and gives visitors a look into the life and legacy of this artist. 
  • Tanglewood: Spread your blanket out and catch a show at this music venue. It’s the summer home of the Boston Symphony Orchestra and boasts an impressive lineup of musicians and performers each year.
  • Ioka Valley Farm: This 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.
  • Outdoor activities: Take a beautiful hike up to the peak of Monument Mountain, or walk the trails of Mount Greylock State Reservation, the first state park in Massachusetts. Ziplining and waters sports are also perfect activities for those looking for a bit more adventure. Berkshire East Canopy Tours offers lots of great zipline rides and tours. 
  • The Mount: This National Historic Landmark celebrates the legacy of Edith Wharton through educational and public programs as well as the conservation and preservation of her estate and gardens. It’s popular year-round, but especially beautiful during the fall at peak foliage time. 

Food & Dining

The Berkshires has become known for its farm-to-table approach to dining. The food culture in the Berkshires focuses on using the best local, organic, and seasonal ingredients to create flavorful dishes that don’t disappoint. From award-winning restaurants to interesting food trails, there’s something to satisfy every craving here. Foodies will enjoy following the Beer & Cider Trail and the Cheese Trail during their stay. Those staying in Berkshires vacation rentals can get out of the house for an evening to enjoy a meal at Table Six. This restaurant combines historical ambiance with fantastic food. At 51 Park Restaurant and Tavern, diners will love the meals cooked from scratch with the freshest ingredients.

Events

Think about visiting the Berkshires during one of the region’s many local festivals. In August, the Rock, Rattle & Drum American Indian Pow Wow is a fun festival with native dancing, music, arts and crafts, and much more. From late-September to early-October, enjoy beautiful foliage and check out the Fall Foliage Festival & Parade in October. It has been drawing crowds for more than 60 years and features seasonal produce, homemade goods, a 5k race, and a fun parade. If you’re visiting during the winter, cheer on amateur athletes at the Bay State Winter Games.

Visit the Berkshires for a charming escape from city life. Whether you’re looking to relax at one of the many Berkshires vacation rentals in a small town atmosphere or take on an outdoor adventures this region has something for everyone.

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