Where to stay in the Berkshires

The Berkshires stretch across Western Massachusetts, conveniently located a few hours from Boston and New York.

In the winter, the Berkshires are home to some of the best skiing, snowboarding, and other winter sports. In the summer, the Berkshires are a popular destination for hiking, camping, fishing, and swimming.

Known for the breathtaking scenery and quaint small-town feel, the Berkshires are a popular destination for tourists from all over. Whether you’re looking to escape the hustle and bustle of city life or simply want to enjoy some of the best nature has to offer, the Berkshires are sure to provide you a fantastic getaway.

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With so many towns and villages to choose from, it can be tough to decide where to stay. To help you make your decision, we’ve compiled a list of the three best places to stay in the Berkshires (in our humble opinion!).

1. South County

Bash Bish Falls State Park is fairly easy to find but the climb down and the subsequent climb out is not an easy proposition. The waterfalls themselves are beautiful and the water was thundering over to the bowl below.

The Berkshires’ South County is home to the towns of Egremont, Alford, Sandisfield, Sheffield, West Stockbridge, Great Barrington, Monterey, and New Marlborough. South County is the largest and most popular destination in the Berkshires, thanks to its convenient location and proximity to major attractions.

South County is home to several ski resorts, including Ski Butternut, as well as lakes, hiking trails, golf courses, and other outdoor activities. Great Barrington, the largest town in South County, is also home to several restaurants, shops, and cultural attractions, including many of our favorite spots for eating.

Some of our favorite destinations include:

  • Monument Mountain – Great Barrington
  • Bash Bish Falls – Mount Washington
  • Mahaiwe Performing Arts Center – Great Barrington
  • Ski Butternut – Great Barrington

Because of its close proximity to so many of the Berkshires’ popular year-round destinations, South County towns and villages are some of the best places to stay in the Berkshires. Whether you are looking for where to stay in the Berkshires in summer or winter, close to town or hidden among the trees, finding a cozy, comfortable spot in South County is a no-brainer and our first choice.

2. North County

North Adams, MA -- 3/13/2017 - MASS MoCA is preparing to open Building 6, a 130,000 square foot expansion that will make it the largest contemporary art museum in the country.  (Jessica Rinaldi/Globe Staff)  Topic: MassMoCA Reporter: Malcolm Gay

North County consists of the towns of Adams, North Adams, Cheshire, Florida, New Ashford, Williamstown, and Savoy. North County is less populated than South County but offers some of the most picturesque landscapes in Berkshire County.

This region of the Berkshires is also known for its charming small towns, scenic mountain views (like Mount Greylock, the tallest peak in the state!), and numerous lakes and rivers. Popular attractions in North County include:

  • Berkshire Museum
  • Clark Art Institute
  • Massachusetts Museum of Contemporary Art (Mass MoCA)

Because of its scenery, it is the perfect area to take in the Berkshires’ fall foliage. If you’re looking for a more rural setting, North County is the place for you. The downside to North County, especially for those coming from New York City is it could add an additional hour plus to your trip, but proximity to some of the cultural attractions like Mass MoCA may make it worthwhile.

3. Central Berkshires

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Home to Lenox, Pittsfield, Dalton, and Richmond, you’ll be right in the middle of the Berkshires and is an ideal place to stay if you want to be close to all the action. This region of the Berkshires is known for its lively towns, world-class museums, and shopping.

Some of the most popular attractions in Central Berkshire include:

Dalton is the smallest town in Central Berkshire but is home to several great restaurants and sights.

Lenox, on the other hand, is one of the Berkshires’ most popular tourist destinations. The most wealthy town in the Berkshires, Lenox is known for its luxury hotels and extravagant summer getaway opportunities. 

Pittsfield, the largest city in Berkshire County, has a lot to offer visitors. Renowned as the cultural capital of the Berkshires, Pittsfield is home to several museums, art galleries, and performance venues. 

Whether you’re looking for a lively setting or a remote summer getaway this may be the perfect place to stay.

So, Where Should I Stay In the Berkshires?

Now that you know a little more about each region of the Berkshires, it’s time to decide where to stay. If you’re looking for a convenient location with easy access to outdoor activities and lively towns, South County is the place for you and where we spend most of our time.

South County provides a great hub and still affords you the easy option to drive to other towns like Lenox, Pittsfield, or North Adams for a lovely day trip. From New Marlborough to Mass MoCa is a little more than an hour drive, making it an easy day trip that you can pair with a hike at Mount Greylock or lunch in Pittsfield (check out Dotties!). 

No matter where you decide to stay, you’ll find that the Berkshires has tons of nooks and crannies of cultural activities, amazing outdoor adventures, and delicious food making you wonder when you can come visit again. 

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