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Great Barrington Massachusetts Vacation Rentals - Cabin
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Great Barrington Cabin
2 BR / 1 BA / Sleeps 5 2 5 2 night min stay
Cabin / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berksh...
Sheffield Massachusetts Vacation Rentals - Home
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Sheffield Home
4 BR / 3.5 BA / Sleeps 10 4 10 4 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Private, 13 Acres, In- Ground Heated Pool, 4 Bdrms, 3&1/2 Baths, Home Office This completely renovated & restored horse barn has been carefully designed, decorated and conceived to guarantee our guests a private...
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Lee Estate
6 BR / 5.5 BA / Sleeps 14 6 14 7 night min stay
Estate / 6 Bedrooms / Sleeps 14
6 bedrooms 5.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Chanterwood is an expansive, light- filled modern home with the luxuries one expects today in a lakefront estate blended with the comfort, casualness and intimacy of its' 100- year old Inn heritage. Sited on 12 acr...
Adams Massachusetts Vacation Rentals - Cabin
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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
Welcome to The Red Pines Lodge! Only minutes away from Castle Rock Lake and 20 min away from Wisconsin Dells. Quiet and secluded. Nestled between the red pine trees. Here you can get away from it all, yet is close enou...
(3) Excellent (3 reviews)
Charlemont Massachusetts Vacation Rentals - Studio
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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 • Washer/Dryer
BREAKING NEWS: Cavalier Cottage has received, for the 2nd consecutive year, two distinguished awards as 'Top Vacation Rental' and 'Rated Excellence' by FlipKey, a division of TripAdvisor. In their own words... 'C...
(2) Excellent (2 reviews)
Pittsfield Massachusetts Vacation Rentals - Condo
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Pittsfield Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • Washer/Dryer
Welcome to our home! This beautiful, luxury unit is fully equipped with everything a family will need for the perfect Mountainside vacation. 3 Bedrooms accommodates 8 guests with all the comforts of home. Master be...
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Great Barrington Home
6 BR / 4.5 BA / Sleeps 12 6 12 7 night min stay
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 4.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park- like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4. 5 bathrooms, sweepi...
Stockbridge Massachusetts Vacation Rentals - Home
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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
Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updat...
(1) Excellent (1 review)
Great Barrington Massachusetts Vacation Rentals - Home
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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
Elegant, contemporary one bedroom house sleeps 4. Great central location. Peace, beauty and convenience. Perfectly located for all Berkshires activities, while still maintaining privacy and quiet. All new construction...
(1) Excellent (1 review)
Lee Massachusetts Vacation Rentals - Home
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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
Enjoy all the Berkshires has to offer in the recently restored and renovated Historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of...
(7) Excellent (7 reviews)
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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
Beautifully remodeled quaint 1930s home overlooking 5 riverfront acres, with all modern amenities including two full bathrooms, laundry facility, internet access, patio and screened in porch with a gas grill for your...
(1) Excellent (1 review)

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. 


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. 


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.


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.