Where to stay in the Berkshires

The Berkshires stretch across Western Massachusetts, conveniently located about three hours from both 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 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.

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 opinion!).

Lay of the land

Before we dive into the list let’s give you a lay of the land. Berkshire county is broken up in three areas that run north to south.

South County

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.

Central Berkshires

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:

The Norman Rockwell Museum
The Sharon Audubon Center
The Berkshire Scenic Railway Museum
The annual Tanglewood Music Festival

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.

North County

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.

Our list: Where to stay in the Berkshires

1. New Marlborough — Best overall

Top of our list of where to stay in the Berkshires is New Marlborough. New Marlborough is tucked away in South County and one of the closest villages in the Berkshires to New York City. New Marlborough is about 10 minutes to Great Barrington and about 30 minutes to places like Tanglewood.

If you’re coming to the Berkshires, chances are you want to be in nature and New Marlborough allows exactly that. You can rent a house, like Oak Hill House, and surround yourself amongst soaring oak trees, babbling brooks, breathtaking views, and still be minutes to all the action. You won’t find chain hotels or bustling streets. Instead what you’ll find are friendly faces, people walking their dogs on the numerous trails and paths, and a quiet sense of community.

Moreover, New Marlborough packs a punch when it comes to food. The seemingly sleepy villages has Gedney Farm and Old Inn on the Green – two of our favorite restaurants in the region. While technically in Southfield, The Southfield Store serves up incredible homemade bake goods and friendly faces and is our go-to morning spot.

With lakes, hikes, serenity, and delicious food New Marlborough is our go to for someone to experience what makes the Berkshires such a delightful place to visit.

2. Lenox — Best for thriving cultural attractions and ritzy downtown

Chances are if you’ve heard of the Berkshires you may be picturing Lenox and the numerous attractions that surround it. From Tanglewood, the storied music venue, to Kripaulu, the massive yoga and health and wellness center, to the Miraval and Canyon Ranch, the gilded age estates turned into luxurious spas.

If you’re looking for a central location that’s a short drive to many of the best attractions in the Berkshires Lenox may be the best place for you to stay. Whereas New Marlborough you’ll find beautiful houses tucked away in the woods, in Lenox you’ll find houses, but more so you’ll likely find hotels – independent and more recognizable brand names that sprinkle downtown and the surrounding streets.

We often consider Lenox to be the cultural hub of the Berkshires with a charming downtown with adorable cafes (we love Haven!) and fancier restaurants.

Overall, Lenox is a fantastic place to stay in the Berkshires, especially if you want a thriving “downtown” feel that you can walk to restaurants, shops and cultural attractions.

3. Stockbridge — Best for small town charm

Stockbridge sits in between Lenox and New Marlborough and similarly has a bit of both towns that make it an excellent place to stay during your trip to the Berkshires. If New Marlborough is the quiet village and Lenox is the bustling, gilded age-reminiscent downtown, Stockbridge delivers a small-town charm that will make you want to grab a scone and a newspaper, sit on a bench in town, and chat up folks walking by.

Downtown Stockbridge has adorable cafes, quirky restaurants, and the infamous Red Lion Inn, an iconic historic landmark that dates back to 1773 (they also serve up a delicious burger). In the summer, park yourself at the crowded bar at the Red Lion Inn, grab a bite and enjoy the people watching to see locals and tourists alike visit this iconic locale.

Stockbridge has cultural attractions, like Naumkeag and the Norman Rockwell museum, a taste of nature at the Berkshire Botanical Garden and the Stockbridge Bowl, one of our favorite lakes in the region.

Stockbridge is a great location to call “home” during your visit to the Berkshires given its balance between downtown and rustic country and proximity to some of the best attractions in the region.

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 and to be surrounded by nature but mere minutes to all the activities, New Marlborough is the place for you and where we spend most of our time.

New Marlborough provides a great hub and still affords you the easy option to drive to other towns like Great Barrington, Stockbridge, West Stockbridge, Lenox, Pittsfield, or North Adams for a lovely day trip. From New Marlborough to Mass MoCa, for example, 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.