Where to Stay in the Berkshires (7 Best Areas & Places)

👉 Jump to: Best Places to Stay in the Berkshires | Neighborhoods & Areas | Tips | FAQ

I went to college in the Berkshire Mountains of Western Massachusetts, and I’ve explored the whole region. I always reminisce about my days exploring the trails of Williamstown because there’s nothing quite like seeing those purple mountains from a summit at twilight.

If it’s your first time visiting the area, I’d recommend staying in Pittsfield because it’s a good central location. The Hotel on North, a trendy boutique hotel, is my top pick in Pittsfield.

You can also enjoy a pleasant stay at The Red Lion Inn, which is my #1 overall hotel pick for its history, New England charm, and other features. It’s located in the town of Stockbridge.

But as you’ll see, there’s no shortage of options in this wonderful rural area of New England. I’ll break down your choices below and give you an honest run-down of the best towns and hotels.

Best Places to Stay in the Berkshires

If you’re short on time, these are my top picks: 

• 🏆 Best Overall Hotel – The Red Lion Inn
• 📍 Best Location – Hotel on North
• 💎 Best Luxury Hotel – The Williams Inn
• ❤️ Best for Couples – 33 Main
• 👨‍👩‍👦 Best for Families – Fairfield Inn and Suites by Marriott Great Barrington
• 🔔 Best Boutique – Stockbridge Country Inn
• ⛷️ Best For Skiing – Jiminy Peak Mountain Resort
• 🥾 Best For Hiking – Tourists – North Adams
• ⛺ Best For Glamping – Huttopia Berkshires
• 🛏️ Best Budget – The Monument Hotel

Click here to see all top The Berkshires hotels or here for apartments.

Ok, now scroll down for a deep dive into the pros (and cons) of each area of the Berkshires: 

7 Best Areas to Stay in The Berkshires

The Berkshires of Western Massachusetts contain seven major towns and cities. These include Pittsfield, North Adams, Great Barrington, Williamstown, Stockbridge, Lee, and Lenox. 

The region is sometimes split into North County (Pittsfield, North Adams, and Williamstown) and South County (Lenox, Lee, Stockbridge, and Great Barrington), with Pittsfield as the rough dividing line.

Pittsfield

👉 Best Area For First-Time Visitors | ✨ Best Pittsfield Hotels: Hotel on North • 33 Main • Holiday Inn Express & Suites Pittsfield-Lenox

Located right between North County and South County, Pittsfield serves as a fantastic home base for travelers with a car hoping to explore the whole region. This is especially helpful for first-time visitors looking for the full Berkshire experience.

Pittsfield is the largest city in Berkshire County and has a vibrant arts scene. One highlight is the gilded-age Colonial Theater.

Downtown Pittsfield is also home to a couple of chic hotels. For instance, Hotel on North is a trendy boutique hotel housed in a 19th-century building that will appeal to modern travelers. 33 Main is a similar chic hotel located nearby that I would recommend as a romantic getaway for couples.

Pros of Staying in Pittsfield:

• Central location in the Berkshires
• The biggest city in the Berkshires
• Lots to see and do

Cons of Staying in Pittsfield:

• Less natural beauty than in the smaller towns
• Industrial aesthetic
• May disappoint when compared to urban areas outside the region

Lenox

👉 Best Area For Art and Music Lovers | ✨ Best Lenox Hotels: The Cornell Inn • The Yankee, Trademark Collection • Brook Farm Inn

Lenox is famous for its summer music festival, Tanglewood. The festival has a long history as a Woodstock-like venue. It is also the summer home of the Boston Symphony Orchestra and hosts frequent classical music shows.

Visitors will find one-of-a-kind boutique and luxury hotels such as the Cornell Inn, three 18th and 19th century mansions situated on four acres of grounds and gardens. 

Lenox’s artistic reputation isn’t just earned by its music scene; Lenox has also been home to writers such as Edith Wharton, whose estate is now a museum. Bibliophiles can even celebrate a love of literature at The Bookstore, which has an attached wine bar called Get Lit.

Pros of Staying in Lenox:

• Proximity to Tanglewood 
• Trendy bars and restaurants
• Luxury accommodations

Cons of Staying in Lenox:

• Need a car to get between Tanglewood, downtown, and The Mount
• South County (including Lenox) is pricey 

Stockbridge

👉 Best Area For a Romantic Getaway | ✨ Best Stockbridge Hotels: The Red Lion Inn • Stockbridge Country Inn • Shaker Mill Inn

Stockbridge has been known as a year-round resort town since the mid-19th century with the advent of the railroad, attracting residents of Boston looking for respite in the country.

Today, Stockbridge still lives up to its reputation as a fantastic vacation spot. It is home to The Red Lion Inn, my top choice hotel in the region due to its history, architecture, restaurant, and music venue.

This quaint town has some of the best tourist attractions in the region, including the Norman Rockwell Museum. Adult visitors in particular will enjoy the museums and scenic pleasures of this small town.

Pros of Staying in Stockbridge:

• Walkable downtown
• Overall best accommodations
• A wide variety of activities

Cons of Staying in Stockbridge:

• Attractions might not interest kids
• South County (including Stockbridge) is pricey
• Fewer highly-rated restaurants

Lee

👉 Best Home Base for the South Berkshires | ✨ Best Lee Hotels: The Black Swan • Quality Inn – Lee • Lakehouse Inn

Between Lenox and Stockbridge is the town of Lee. Although it’s quieter than the other two, it is considered the “Gateway to the Berkshires” because it’s the first exit off I-90 approaching the mountains.

Some highlights of Lee include the outlet stores and the downtown area, which contains the highest wooden church steeple in the United States.

Couples or solo travelers looking for a serene escape should consider Lakehouse Inn. It is an adults-only retreat and the only hotel on Lee’s Laurel Lake. They offer complimentary kayaking and paddleboarding. The hotel pitches itself as offering “kind, cozy, and chill” vibes. A kid-friendly alternative is The Black Swan, also located on the banks of Laurel Lake.

Pros of Staying in Lee:

• Walkable downtown with great architecture
• Authentic, local vibes
• Easy access to interstate and other South County towns

Cons of Staying in Lee:

• Fewer indoor attractions/museums
• Fewer hotel options
• Relatively pricey

Great Barrington

👉 Best Area For Families | ✨ Best Great Barrington Hotels: Fairfield Inn and Suites • Granville House • Holiday Inn Express • The Monument Hotel

Also in South County, Great Barrington is where I’d tell families with kids to stay instead of nearby Stockbridge and Lee, which have more to offer adults.

Great Barrington’s key attraction is Ski Butternut, one of several skiing resorts in the Berkshires. It has slopes that are great for beginners, a family-friendly atmosphere, and snow tubing. Nearby Lake Mansfield has ice skating in the winter and swimming in the summer.

Great Barrington also has several budget-friendly and family-friendly hotels. The Fairfield Inn and Suites by Marriott offers family rooms and suites as well as a pool, making it my top recommendation for families. Granville House also offers family rooms in a large, historical home.

Pros of Staying in Great Barrington:

• Kid-friendly outdoor activities
• Budget-friendly hotels
• Excellent restaurant and bar options

Cons of Staying in Great Barrington:

• Fewer indoor attractions/museums
• Fewer high-end hotel options

North Adams

👉 Best Area For Bohemians and Hikers | ✨ Best North Adams Hotels: Tourists • Hotel Downstreet • The Trail in Adams

North Adams is a small, historic milling and factory town with a rapidly evolving artistic and cultural scene.

North Adams is home to MASS MoCA, one of the largest contemporary art museums in the country. It is housed in an old print works building. If you’re an art lover, you may choose to stay at The Trail in Adams, an “art hotel” that surrounds you with beauty. They also offer a gluten free and vegetarian breakfast.

North Adams is also a great home base for anyone interested in accessing the Appalachian Trail and Mt. Greylock, the tallest peak in Massachusetts. The Gould Trail in Adams is a great way to get to the summit, but it’s not an easy hike.

Travelers interested in embracing the adventurous spirit of North Adams should check out Tourists, which bills itself as a “riverside retreat inspired by the classic American roadside motor lodge.” The hotel property contains hiking trails and 80 acres of forest and offers an “arts and adventure” program with complimentary guided activities for guests.

Pros of Staying in North Adams:

• Great art scene, including the world-class MASS MoCA
• Proximity to the Appalachian Trail and Mt. Greylock trailheads
• Generally more affordable than the South County towns

Cons of Staying in North Adams:

• Industrial factory aesthetic
• Not very walkable

Williamstown

👉 Best Area For College-Town Vibes | ✨ Best Williamstown Hotels: The Williams Inn • Clover Hill Farm & Country Inn • Maple Terrace Motel

Furthest north on our list, near the borders of Vermont and New York, lies Williamstown, a beautiful college town. It is home to my alma mater, Williams College.

Like North Adams, Williamstown offers great access to the Appalachian Trail and even the Long Trail of Vermont, making it a fantastic destination for backpackers. It is also an easy drive to Jiminy Peak, the largest ski resort in southern New England.

Couples and adults might enjoy returning from a day of hiking or skiing to the upscale Williams Inn. It is located right on Spring Street, a small downtown area just a few blocks from the college campus. Families with kids should check out  Clover Hill Farm & Country Inn, which offers suites and family rooms

While you’re in Williamstown, make sure to visit the Clark Art Institute. This world-class museum and research center made our list of top attractions in Massachusetts!

Pros of Staying in Williamstown:

• Stunning natural beauty
• A beautiful college campus
• Easy access to Vermont and New York–even on foot!
• Great for fall foliage

Cons of Staying in Williamstown:

• Furthest from the attractions of South County
• Generally a sleepy, quiet town
• The college makes up much of the town

Tips for Staying in the Berkshires

Expect cold weather

The Berkshires are colder than you might expect due to the mountainous terrain! This also means that some of the roads to higher elevations (such as within parks) shut down earlier in the season than you might expect.

Pack for cold weather

If you’re traveling at a time when there might be snow (the end of October through the end of April), consider packing or procuring some safety gear such as crampons/snow grips for your shoes (devices that increase traction on ice) and Hot Hands for inside your gloves and socks.

Check the weather for the town you’re in

Due to the lake effect (the way that terrain changes impact weather patterns), the Berkshires can experience heavy snow in one town and no snow in the adjacent town. When you check the weather, be sure to be specific.

Visit during the fall–but plan ahead!

The Berkshire Mountains have some of the most stunning foliage I’ve seen in New England, and that makes the region a popular destination for leaf peepers. Be sure to make hotel and restaurant reservations well in advance.

Have a plan for the kids

The Berkshires are beautiful, relaxing, and serene–and they might be under-stimulating for your young ones. Be sure to plan a few kid-friendly activities and adjust your expectations accordingly if you take the whole family on vacation.

FAQs

What are the best areas to stay in the Berkshires for first-timers?

Pittsfield is the best place for first-timers to stay in the Berkshires due to its central location.

What is the best part of the Berkshires to stay with kids? 

Great Barrington is the best part of the Berkshires to stay with kids because of its proximity to Ski Butternut and Lake Mansfield.

What is the best part of the Berkshires to stay for hikers? 

North Adams is the best location in the Berkshires for hikers due to its proximity to the Appalachian Trail and paths that will lead to the summit of Mt. Greylock.

Where is the best skiing in the Berkshires?

Jiminy Peak is the best ski resort in the Berkshires and is the largest ski area in southern New England. Ski Butternut is the best ski area for families due to the diverse array of slopes.

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Whether you want to hike, ski, or just relax in nature, I hope this guide has made you excited to explore the Berkshires of Western Massachusetts! You’re sure to love what this region has to offer! Before you go, be sure to check out Claudicet’s guide to the best places to visit in Massachusetts.