The Berkshires, Massachusetts, quickly puts visitors under a spell with its tree-covered hills and gripping culture. Lenox and Stockbridge, nestled side by side, are two gorgeous options for where to stay in The Berkshires that abound with both. Located at the region’s heart, these towns also make excellent bases for day trips up north or down south.
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- Superb picks for first timers, Lenox and Stockbridge are surrounded by nature, boast unique sights and provide a central vantage point. See The Constance (Lenox) and The Red Lion Inn (Stockbridge).
- Northern Berkshires, including Williamstown and North Adams, is prime territory for leaf peepers. Mount Greylock and the Mohawk Trail create unlimited peeping opportunities in fall.
- You can drive from Williamstown (north) to Great Barrington (south) in an hour, meaning that all area attractions are within day trip distance no matter where in The Berkshires you stay.
Staying in Lenox makes things easy for you. This cultivated town not only holds some of The Berkshires’ best attractions but also puts you centrally in the region, meaning day trip opportunities are excellent.
New Yorkers and Bostonians have long soughed inspiration (and cooler summer temperatures) in The Berkshires. Have a picnic while enjoying the most harmonious big-city bunch, the Boston Symphony Orchestra, at their Lenox summer venue, Tanglewood.
A Lenox work of art, the 1902 Mount estate was carefully designed and lived in by celebrated author Edith Wharton. Come here to marvel at the majestic mansion and grounds inspired by Europe but adapted for America — you don’t need to be a fan or history buff to appreciate it.
On top of those iconic draws, be sure to stroll the well-polished Downtown Lenox. An area that feels of just the right size, it’s big enough to offer the dining, shopping and sleeping opportunities you need without losing that lovely small-town charm.
Best hotels in Lenox
- The Constance – In Lenox’s heart, the elegant Constance appears like a white fairytale castle a la New England. Embrace uniquely decorated guest rooms and succumb to the inviting veranda with plenty of room to sit down.
- The Cornell Inn – The Cornell Inn boasts three tastefully restored buildings from the 1700s and 1800s. Savor a warm vibe and free hearty breakfast — within walking distance of Lenox shops and restaurants.
- Marriott Lenox – This dutiful big-chain hotel covers all the essentials. Appreciate clean rooms and top facilities, including an indoor swimming pool, hot tub and fitness center, just a 1.5-mile (2.4 km) ride from downtown Lenox.
- Seven Hills Inn – Where to stay near The Mount? Sprawling Seven Hills Inn invites you to stay next to (literally) the breathtaking Edith Wharton property that people flock to from far and wide.
Ready to step into a Norman Rockwell painting? The Berkshires’ small-town, big-nature theme is as evident as ever in Stockbridge, a sleepy town lying a 10-minute drive south of Lenox.
Picture a Main Street lined with green lawns, rising trees and idyllic homes. At the heart of it all, a handful of eateries, shops and a historic hotel, The Red Lion Inn, backdropped by imposing wooded hills await.
The quaint Downtown Stockbridge scene, in holiday mood, was made famous and immortalized by America’s favorite illustrator, Norman Rockwell, in his 1967 painting “Stockbridge Main Street at Christmas”.
While Rockwell lived on connecting South Street, visit the higher-elevated Norman Rockwell Museum, overlooking leafy Housatonic River Valley, to absorb his engaging art. One of the Berkshires’ biggest attractions, it harbors 998 original works (including that Main Street painting) and in total over 100,000 items.
Best hotels in Stockbridge
- The Red Lion Inn – Sleep in a beloved Norman Rockwell motive. Choose from 82 rooms at the historic main inn, roomy village houses and the nearby (within 2 minutes’ walk) Maple Glen complex, offering contemporary lodging.
Should I stay in Lenox or Stockbridge? These towns are both excellent options for where to stay in The Berkshires. However, keep in mind that Lenox (good or bad) is bigger (or less small) with more downtown distractions and accommodation options.
There’s a West Stockbridge too: Aptly named, West Stockbridge nestles to the west of Stockbridge. In this off-the-beaten-path version, the Shaker Mill Inn presents well-equipped suites.
Expect to run into students and professors as well as visiting parents and alumni in this northern Berkshires home of the 1793 Williams College. Williamstown is built around its historic university, with campus buildings seamlessly dotting the downtown area.
Amid youthfulness, sample masterpieces at the Sterling and Francine Clark Art Institute, or just the Clark, with French Impressionism as its most shining category. Be sure to allow time for the outside collection of installations spread across 140 undulating acres.
At the town’s heart, Williams College Museum of Art boasts 15,000-plus works. Marvel at mind-bending contemporary art; then digest it on nearby Spring Street, lined with atmospheric restaurants and shops.
Up for some hiking? The Appalachian Trail, connecting New England with the Deep South, runs right through Williamstown.
Best hotels in Williamstown
- The Williams Inn – Check in at the modern 64-room Williams Inn to have the best of Williamstown at your fingertips. But if you just want to stay in, sit down for dinner at the on-site Barn Kitchen & Bar.
- Maple Terrace Motel – Maple Terrace Motel oozes countryside charm. Think a blend of New England and the traditional roadside motel.
- Willows Motel – Your hard-earned dollars last longer at Willows Motel, providing basic but clean rooms at a convenient location for exploring northern Berkshires.
It took a while for North Adams to be approved for The Berkshires’ swanky club of art communities. However, what was a city focusing on mass production until the 1980s nowadays is a powerful creative force, one that’s here to stay.
Its centerpiece, Massachusetts Museum of Contemporary Art occupies a sprawling 26-building complex, once dedicated to manufacturing, on the Hoosic River in Downtown North Adams. Be amazed by the airy space filled with boundary-crossing painting, sculpture, music, dance, film, photography and theater — it’s all here.
For awe-inspiring nature, take a 10-minute drive south to find the Adams without a north, resting directly below Mount Greylock, Massachusetts’ tallest peak; leisurely cruise or hike up to the 3,489 feet (1,063 m) summit, where unobstructed 90-mile views await.
Best hotels in North Adams
- The Porches Inn – These aesthetically pleasing Victorian rowhouses set the vibe just right for MASS MoCA, which you reach in 5 minutes’ walk. Bonus features: The outdoor pool deck complete with a sauna and on-site recording/gathering venue, Studio 9.
How about some roadtripping? The scenic Mohawk Trail, peaking during the fall foliage season, is a bucket-list New England drive. Williamstown marks its western end; North Adams spreads out right along it.
You can upsize your Berkshires getaway too. Pittsfield didn’t get the memo: This 40,000-plus-people city, the Berkshires’ biggest, lacks the signature small-town character of the region.
Berkshire County’s seat, Pittsfield has a downtown area dotted with grand buildings erected between the mid-1800s and early 1900s, such as the educational Berkshire Museum and, if you prefer a show, Colonial Theatre. Here, choose from an array of eclectic cafes and dining opportunities, completing the city experience.
Then there’re the big-ticket items on Pittsfield’s outskirts: Discover the Hancock Shaker Village, or “The City of Peace” as its religious population used to call it; and learn about the author of Moby Dick, Herman Melville, at his yellow-painted 1785 Arrowhead house.
Best hotels in Pittsfield
- Hotel on North – Experience the Berkshires’ finest city stay. Set in a pair of 19th-century buildings in Downtown Pittsfield, boutique-style Hotel on North offers a refreshing contrast to The Berkshires’ otherwise small-town dominance.
- Berkshire Mountain Lodge – Handily sitting just off US Route 20, the Berkshire Mountain Lodge provides spacious condo-style accommodations with kitchen. Spread out in your suite or take a dip in the indoor swimming pool. Bonus: This is a 5-minute ride from Herman Melville’s Arrowhead.
Rather stay on a lake? Then consider the Lakehouse Inn, located between Lenox and Lee. The vibe is peaceful and views of Laurel Lake stunning — the Mount mansion hides across the water.
Welcome to the hub of the southern Berkshires, a getaway destination constantly tempting you. Charismatic Great Barrington invites you to roam without knowing what the next great find will be.
Browse independent stores, recharge at quirky coffee hangouts and, when hunger calls, sample the best of farm-to-table dining on Main and Railroad streets. To base yourself right here, check in at The Barrington, sitting at the most sought-after location in town.
Crave for nature? Aim at the stone’s-throw-away River Walk, tracing Housatonic River. Or make the 4-mile drive to 1,642-foot Monument Mountain; hike up to marvel at views of Housatonic River Valley, Mount Greylock and the Catskill Mountains — bring your camera.
Best hotels in Great Barrington
- The Barrington – This refined seven-suite hotel boasts an unbeatable location at Great Barrington’s heart — act swiftly if there’s availability on your dates.
- Granville House – Just outside town, the stately white pillars of the Granville House evoke feelings of the American South. Step inside to find five tasteful guestrooms and sociable common areas ranging from a parlor with pool table to a music room with vinyl albums to, of course, a wraparound porch equipped with rockers.
Where to stay in The Berkshires FAQ
The Berkshires covers the westernmost part of Massachusetts. Cities and towns here include Lenox, Stockbridge, West Stockbridge, Williamstown, North Adams, Pittsfield, Lee and Great Barrington.
Lakehouse Inn, facing beautiful Laurel Lake, makes an excellent place to stay in The Berkshires in summer. Other great places to enjoy summer, maybe sitting on a soothing porch, are The Constance, in Lenox, and Granville House, in Great Barrington.
As summer turns into fall, The Berkshires explodes in yellow and orange colors. A favorite location to take it in is northern Berkshires, including Williamstown and North Adams — put Mount Greylock and the Mohawk Trail on your itinerary.
Stay at The Red Lion Inn in Stockbridge to experience one of America’s most famous winter streetscapes first hand. Norman Rockwell immortalized the delightful downtown area hotel in his 1967 painting “Stockbridge Main Street at Christmas”.