Berkshires Apartment Rentals & Vacation Rentals - 11 Rentals Available

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1 / 14

Great Barrington Home
1 BR / 1 BA / Sleeps 4 1 4 Min stay varies
Home / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"We were truly delighted to find such a spacious, clean, contemporary, sun- lit, apartment so near everything we come to the Berkshires for: Tanglewood, Jacob's Pillow, Great Barrington's charming night life, hiking, and simply beautiful surroundings...."
- Stephanie Austin, New York, New York
(1) Excellent (1 review)
1 / 23

Adams Cabin
4 BR / 2.5 BA / Sleeps 10 4 10 Min stay varies
Cabin / 4 Bedrooms / Sleeps 10
4 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"We stayed with 10 guys for a ski trip. House is 50 min. away from the cascade mountain, which was only bad part, but other than that it was perfect. Pool table, grill, fire pit and a ton of room was a perfect place to hang out! If you like quiet ..."
- Milos Dragicevic, Chicago Il
(3) Excellent (3 reviews)
1 / 47

Stockbridge Home
3 BR / 2 BA / Sleeps 6 3 6 2 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This was a great property/ location in Stockbridge, MA for 3 couples to meet for a long fall weekend visit to the Berskshires. The house has 3 bedrooms, 2 large full baths, is homey, well equipped & mostly updated. Plenty of space at the dining ..."
- Lori Rosenthal Stein, East Aurora, NY
(1) Excellent (1 review)
1 / 24

Lee Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Our stay at Mary Lincoln's South Lee school house was wonderful. It was ideal for our family members to get together for a reunion. It was very clean, open and spacious, well designed and decorated. Everything was there that we needed. The bedrooms..."
- Rebecca Lincavicks, Connecticut, Maine, and New York.
(8) Excellent (8 reviews)
1 / 29

Charlemont Studio
Studio / 1 BA / Sleeps 4 0 4 2 night min stay
Studio / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
High Speed Internet • Microwave • Air Conditioning
"Great place to recharge, very pet friendly. Loved the setting and the scones, baked fresh every morning."
- Mike Reinhard, Concord, CA
(2) Excellent (2 reviews)
1 / 20

Stockbridge Home
3 BR / 2 BA / Sleeps 5 3 5 7 night min stay
Home / 3 Bedrooms / Sleeps 5
3 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"We could not have asked for more with this perfect location and all the attention to detail. 3 comfortable bedrooms and 2 full baths made for a very comfortable stay for 5 people. There is plenty of room to spread out and find a quiet place to read or..."
- Bee Webster Dietemann, Texas
(1) Excellent (1 review)
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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.