Where to Stay in the Berkshires → 6 BEST Areas (With Prices)

The Berkshires are highlands in Western Massachusetts that are well beloved for their stunning landscapes and wide range of outdoor activities. Whether you want to go hiking in summer, admire the fall foliage, or hit the skiing slopes in winter, the first thing you need to decide is where to stay in the Berkshires! 

I’ve researched and compared all towns in the Berkshires and created a list of the 6 ultimate spots for your stay. 

The town of Lenox is the best place to stay in the Berkshires, especially if you’re visiting the region for the first time. In Lenox, you’ll find a variety of cool attractions, great restaurants, and some of the top Berkshires hotels. 

For each town recommended in this post, I also handpicked the best hotels and inns in each price category so you can have an unforgettable Berkshires vacation. Whether you want to splurge or visit on a budget, I have a recommendation for you! 

Regardless of which town and hotel you pick, you need to hurry up and make a reservation. The Berkshires are a year-round destination, and the best accommodations are quick to sell out! 

Let’s jump right in!

Quick Picks for Your Stay

Want to book now? These are the best Berkshires hotels situated in Lenox, MA: 

Here’s a map of the Berkshires showing all the towns featured in this post: 

1. Lenox – where to stay in the Berkshires for the first time

The historic town of Lenox is the hub of activity in the Berkshires. Located South of the mountain ranges, this town has a charming atmosphere and plenty to offer! If you’re interested in cultural activities and history and you also want to be well connected to the entire area, Lenox is the best town to stay in the Berkshires! 

In fact, here, you will find countless art galleries and interesting attractions like the ancient Lenox Library (map), the Ventfort Hall Mansion & Gilded Age Museum, and the Boston Symphony Orchestra, a hub for theater and visual arts.

If you’re a Shakespeare fan, then you absolutely have to attend a performance at Shakespeare & Company, a live theater that puts on both classic and contemporary iterations of the plays. 

Another must-visit while in Lenox is The Mount, Edith Wharton’s Home that’s been transformed into a museum and also hosts a bookstore and a cafe. And if you’re into trains, you should check out the Berkshire Scenic Railway Museum where you can tour the rail yard and learn more about the history of rail travel in the region. 

But if you just want to spend a lazy afternoon, the town offers many creative boutiques to do some shopping and amazing restaurants where you can enjoy a delicious meal. And while you’re wandering around Lenox streets, you won’t be able to stop gazing at the amazing architecture of the buildings!

And if all this wasn’t enough, from Lenox, you can access so many outdoor experiences, like exploring the tree-lined trails in Kennedy Park (map) and hiking in Mass Audubon’s Pleasant Valley Wildlife Sanctuary (map), where you can also meet the resident beavers! 

For your stay in Lenox – actually, anywhere in the Berkshires – I highly recommend renting a car if you didn’t drive there in your own vehicle. The region has so much to offer, and you can’t fully experience it without driving, so be sure to pack your driver’s license. 

NOTE: Lenox is a bit more upscale than the other towns featured in this post. So, you can expect to pay a bit more for accommodation, as well as for activities and dining out.

Other accommodation options in Lenox

Things to do in Lenox

• Visit the Lenox Library and the Ventfort Hall Mansion & Gilded Age Museum
• See an outdoor concert at the Boston Symphony Orchestra
• Attend a theater performance at Shakespeare & Company
• Spend a few hours exploring The Mount, Edith Wharton’s Home
• Learn some fun facts at the Berkshire Scenic Railway Museum
• Go hiking in Kennedy Park or Mass Audubon’s Pleasant Valley Wildlife Sanctuary

2. Stockbridge – the most laid-back area in the Berkshires

The charming town of Stockbridge, located a 10-min drive Southwest of Lenox, is known as the quintessential small town of America. It has a very laid-back vibe and is the perfect place if you want to relax and enjoy some peace and quiet! 

The town is famous for being home to the artist Norman Rockwell, and while you’re here, you absolutely have to visit the Norman Rockwell Museum! The museum has a significant collection of the artist’s original works and memorabilia, and it’s a great place to spend a few hours. 

But that’s not all! Stockbridge has plenty more to offer. You absolutely have to stroll down the picturesque Main Street (it’s actually featured in one of Rockwell’s paintings) and tour Naumkeag, a 19th-century home with lavish interiors and gorgeous gardens. 

For more cool places to visit in Stockbridge, I’d recommend Chesterwood, the former home of famed sculptor Daniel Chester French, and the Berkshire Botanical Garden, where you can enjoy a leisurely stroll or even a picnic. 

However, if you prefer to spend time outdoors, you should definitely hike Monument Mountain (map). There are plenty of good hiking trails to reach the summit, and you can admire lush vegetation and waterfalls along the way. Once you reach the top, you can relax and enjoy the stunning view. 

Music lovers will definitely appreciate Tanglewood (map), an outdoor music venue; during summer, you can attend a performance and even lay down a blanket and sit on the grass. I highly recommend doing this if you’re visiting during the warmer months – it’s a magical experience!

Stockbridge doesn’t have as many accommodation and dining options as other towns in the Berkshires, meaning it’s not as crowded as some other places – ideal for relaxing! 

Other accommodation options in Stockbridge

Things to do in Stockbridge

• Admire the art at the Norman Rockwell Museum
• Stroll along Main Street and admire the architecture
• Visit Naumkeag and Chesterwood
• Spend a few hours exploring the Berkshire Botanical Garden
• Stop by the National Shrine of The Divine Mercy (map)
• Hike up to the summit of Monument Mountain
• See a performance under the open sky at Tanglewood

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3. Adams & North Adams – where to stay in the Berkshires with the family

Adams and North Adams are 2 adjacent towns situated approximately 25 miles (40 km) North of Lenox (about a 45-min drive away). Both of these towns have a lively atmosphere and offer a good range of things to do, which makes them the best places to stay in the Berkshires if you’re traveling with family. 

The town of Adams is home to several notable attractions, but probably the most popular one is the Susan B. Anthony Birthplace Museum. The museum hosts exhibitions on the life of Susan B. Anthony and covers an important period in US history – in my opinion, it’s a must-visit! 

The Veterans War Memorial Tower (map) is another notable Adams landmark – you can take the stairs up to the top of the tower and enjoy a great view of the surrounding area. The tower is situated at the summit of Mount Greylock, the highest peak in the area and a great place to do some hiking. 

If you decide to hike in the Mt. Greylock area, there are plenty of different trails you can take. The trails have different difficulty levels, but none is super easy, so I don’t advise going with very young kids. 

In North Adams, the top attraction is the MASS MoCA, a widely known contemporary art museum. Even if you’re not super into art, I suggest you visit this museum – it’s very innovative and has many different (and cool) exhibitions. 

Much like Adams, North Adams also provides plenty of opportunities for outdoor recreation. You should definitely visit Natural Bridge State Park (map); it has various walking paths and trails, plus picnic spots, making it a great place to spend a day with the family. 

Other accommodation options in Adams

Things to do in North Adams

• Visit the Susan B. Anthony Birthplace Museum
• Take the stairs to the top of the Veterans War Memorial Tower and enjoy the view
• Go up to Mount Greylock and explore one of the hiking trails in the area
• Enjoy a Sunday brunch at Freight Yard Pub (map)
• Admire the exhibitions at the MASS MoCA
• Have a picnic in Natural Bridge State Park

4.  Great Barrington – best area in the Berkshires for nature

If you drive for 25-min to the Southwest of Lenox, you will find the vibrant town of Great Barrington. The town is blessed with breathtaking nature, striking mountain views, and many outdoor activities in the close surroundings!

One of the most popular destinations for tourists in Great Barrington is the magnificent Monument Mountain (map), also easily accessible from Stockbridge. Even if you don’t want to climb all the way to the mountain summit, you can explore other trails in the Monument Mountain Reservation (map) and even go skiing in the winter. 

FUN FACT: The famous American authors Herman Melville and Nathaniel Hawthorne met while hiking Monument Mountain in 1850. A storm forced them to take shelter in a cave, where they had a discussion that inspired Melville to write the famous novel Moby Dick. 

Here, you can stay in touch with nature literally all year round, having access to ski slopes like the Butternut Ski Area and Tubing Center (map) during winter. In summer, you can explore many hiking trails, such as the Housatonic River Walk (map) or the walking path in the forest around Lake Mansfield (map)! 

In case you’re still wondering what to do in the Berkshires, and specifically in Great Barrington, you should check out the Great Barrington Farmers Market (map) that takes place every Saturday between May and November. I also suggest grabbing something to eat from Guido’s Fresh Marketplace (map), an artisanal grocery store. 

If nature and peace are what you’re looking for, Great Barrington is where you’ll find it!

Other accommodation options in Great Barrington

Things to do in Great Barrington 

• Hike up to the summit at Monument Mountain
• Explore some of the trails in the Monument Mountain Reservation
• Hit the slopes at the Butternut Ski Area and Tubing Center
• Trek along the Housatonic River Walk and the trail around Lake Mansfield
• Visit the Great Barrington Farmers Market
• Get some groceries or a bite to eat from Guido’s Fresh Marketplace

5. Williamstown – where to stay for art enthusiasts

The Berkshires, MA, are well known for their rich cultural and art scene, and no town shows it better than Williamstown. Situated a 50-min drive North of Lenox, Williamstown has that small-town, cozy vibe and is a great place to learn more about the art scene in the region. 

The first stop on your Williamstown visit has to be the Clark Art Institute. This museum has a vast collection of 19th-century art, from various American and European artists – a dream come true for any art lover! 

Your next stop should be at the Williams College Museum of Art, a free museum that boasts a large modernist collection. In the evenings, you can see a movie at Images Cinema (map), an independent movie theater that also displays free outdoor movies during the summer months. 

If you happen to be in Williamstown during July or August, you need to attend at least one performance at the Williamstown Theatre Festival, which puts on original plays as well as reimagined classics. 

Finally, you can’t leave Williamstown without exploring Spring Street, with its many shops, eateries, and cafes. Stop for a coffee at Tunnel City Coffee (map), then grab a bite to eat at the Purple Pub (map). And if you feel like it, you can even hop on over to Vermont or New York – Williamstown is situated right on the state lines! 

Other accommodation options in Williamstown

Things to do in Williamstown

• Admire the collection at the Clark Art Institute
• Visit the Williams College Museum of Art
• Catch a movie at Images Cinema
• See a performance at the Williamstown Theatre Festival during July and August
• Explore Spring Street and grab coffee at Tunnel City Coffee
• Have lunch at the Purple Pub
• Plan a day trip to Vermont or New York

6. Pittsfield – where to stay in The Berkshires on a budget

Pittsfield is the largest town in The Berkshires, located just a 15-min drive North of Lenox. Even though it’s the largest town in the region, Pittsfield has a very serene atmosphere and it’s actually the most affordable place to stay in the Berkshires. 

Compared to most of the towns on this list, Pittsfield is not as popular among visitors, so don’t have to worry about the crowds. Also, you don’t have to worry about being bored – the town has plenty to offer! 

The Berkshire Museum is THE place to visit if you’re traveling with kids. This is both a natural history and an art museum and offers many kid-oriented activities. Another museum you shouldn’t miss is Herman Melville’s Arrowhead, situated in the author’s former home, where he wrote his novel Moby Dick. 

If you’re a history buff, I’m sure you’ll enjoy the Hancock Shaker Village (map), located on the outskirts of Pittsfield. This is a living history museum that allows you to explore the restored historic buildings and participate in cool, unusual activities like farming. 

Skiing enthusiasts are also drawn to Pittsfield! The Bousquet Mountain Ski Area is one of the most popular ski spots in the Berkshires, and it’s open year-round. So, even if you’re visiting in summer or autumn, you can attend a concert there or enjoy a meal at the restaurant. 

For all outdoor lovers, there’s the Pittsfield State Forest (map) with its numerous hiking trails and the Ashuwillticook Rail Trail (map), which is the ideal spot for biking. 

And in case you’re on the hunt for evening activities, I’d recommend seeing a play at the Boyd-Quinson Theater or a movie at the Phoenix Theatres Beacon Cinema. 

You can also have dinner at one of the many Pittsfield restaurants. I particularly recommend dining in a farm-to-table restaurant, like The Marketplace Cafe (map), which offers fresh and delicious food. 

Other accommodation options in Pittsfield

Things to do in Pittsfield

• Take the kids to the Berkshire Museum
• Visit Herman Melville’s Arrowhead
• Spend a few hours exploring the Hancock Shaker Village
• Hit the slopes at the Bousquet Mountain Ski Area
• Explore the trails in Pittsfield State Forest
• Go on a bike ride along the Ashuwillticook Rail Trail
• See a play at Boyd-Quinson Theater or a movie at Phoenix Theatres Beacon Cinema
• Enjoy a farm-to-table meal at The Marketplace Cafe

BONUS: Best campsites in the Berkshires, MA

Even though the Berkshires might seem like a more upscale destination, they’re also a great spot for budget travelers – for example, campers. Camping is quite popular in the region, so if you want to set up your tent on your Berkshires vacation, here are the best campgrounds in the area:

• Mt. Greylock Campsite Park – with 47 RV campsites and 39 tent sites, great facilities, including a camp store, this campground is one of the best and most popular places to camp in the Berkshires, with prices of US$35/night. 
• Historic Valley Campground at Windsor Lake – situated on Windsor Lake, this campground has 100 sites and welcomes RV, camper, and tent campers, with prices starting at US$25 per night. 
• Bonnie Brae Campground – this campground and RV park is located near Pittsfield and offers cabins and trailers for rent, as well as RV and tent sites. Prices start at US$45/night and include free Wi-Fi, hot showers, and more! 
• October Mountain State Forest – at this campground, there are 44 sites as well as 3 yurts that can accommodate 4 to 6 people. But keep in mind that there are no electric hookups. Prices can be as low as US$17/night. 

FAQs about where to stay in the Berkshires

🗺️ Where are the Berkshires?

The Berkshires are located in Western Massachusetts, New England, between the Housatonic River and the Connecticut River.

📍 Which is the best place to stay in the Berkshires?

The best place to stay in the Berkshires is Lenox, offering access to many outdoor activities and interesting attractions, plus amazing hotels like the Hampton Terrace Inn and The Cornell Inn. 

🧳 Are the Berkshires worth visiting?

Yes! The Berkshires are definitely worth a visit, with their many cool museums, hiking trails, ski slopes, and rich cultural scene. 

☀️ Where to stay in the Berkshires in summer?

The best place to stay in the Berkshires in summer is Stockbridge, home to Tanglewood, an outdoor music venue, and the Berkshire Botanical Garden, the perfect spot for a picnic. Stay at the Stockbridge Country Inn or The Red Lion Inn. 

📅 What is the best time to visit the Berkshires?

The Berkshires is a year-round destination, but summer is especially popular as that is when you can make the most of the hiking trails in the region, as well as cool festivals and farmers’ markets. 

🏛️ What is the largest town in Berkshire County, MA?

The largest town in the Berkshires is Pittsfield, home to a couple of great museums, a ski center, amazing farm-to-table restaurants, and budget-friendly hotels like the Hotel on North and Hilton Garden Inn. 

💑 Where to stay in the Berkshires for couples?

The towns of Adams and North Adams are a great spot for a couples’ getaway to the Berkshires. You can stay at the romantic and luxurious Tourists and the lovely B&B The Trail in Adams. 

🌟 What are the best 5-star hotels in the Berkshires, Massachusetts?

There are no 5-star hotels or resorts in the Berkshires, but there are quite a few luxury hotels and upscale inns for a comfortable stay, such as the Hampton Terrace Inn in Lenox and The Barrington in Great Barrington. 

Final words on the best places to stay in the Berkshires

We’ve reached the end of my comprehensive guide on where to stay in the Berkshires! Now, you’re familiar with all the top towns in the region and all the best hotels, so it’s time to make a decision!

However, if you’re having trouble choosing a Berkshires hotel, here are my 2 favorite options, both situated in Lenox: 

• Hampton Terrace Inn – a 4-star hotel with an outdoor pool, rooms decorated with antique furnishings, and a rich and delicious breakfast
• The Cornell Inn – a lovely inn with a bar, concierge services, and free parking

Whatever hotel you pick, make sure to book in advance to secure your spot and get the best deals! You don’t want to miss out on the best hotels or pay a higher rate than you need to!

If you have any questions about your stay in the Berkshires, please leave me a comment. I look forward to hearing from you and answering your questions! 

Have a great holiday,

Hristina

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