If you wanted to argue that the Berkshires are New England’s best-kept gem, I’d agree.
To be fair, it might not be considered a hidden gem given its large size and well-respected reputation. The Berkshires, in case you’ve missed out, are a hilly and forested region located in Western Massachusetts and parts of Connecticut.
The Berkshires are actually a subrange of the Appalachian Mountains. It’s known for its \mature forests. In fact, it’s one of The Nature Conservancy’s 12 Last Great Places.
Aside from its lovely natural setting, the Berkshires are known for their historical and cultural small towns, unique community events and festivals, summer theatre performances, modern art museums, and luxury dining and shopping options.
I’ve thoroughly enjoyed every trip I’ve taken to the Berkshires. (Except for the ticks—though that’s a New England-wide issue.)
Not only were these trips full of small-town whimsy and relaxing forest strolls, but there was also a proud and dedicated sense of ownership over each locale.
The homes, in particular, caught my attention.
From modern ranches to stately mansions to snug cottages, the Berkshires have it all. But if you want to get the most out of your Berkshires trip, I suggest staying in a cozier abode.
Here are the best Berkshire cottages that you’ll want to come back to.
Best Berkshires cottages
Best family pick: Entire Cottage in Canaan
This cottage has everything you need for a great glimpse into life in the Berkshires—including a lakefront location on Queechy Lake.
In warmer months, you can take advantage of the dock and swimming area. In colder months, you can curl up on the deck to enjoy the forest with a fire crackling at your feet.
Though it’s ideal for families (the rental sleeps six in three rooms), it’s also great for those who like to fish or otherwise get out on the water.
Best classic feel: Netherwood – North Adams Guest House
North Adams is one of the best places to be in the Berkshires if you want to enjoy community events in one of its most picturesque small towns.
The Netherwood cottage isn’t too bad, either. Its interior has a classic, low-key cottage design, while its exterior has iconic red panels. If you love that Americana feel, here’s your perfect cottage pick.
The home’s deck is perfectly situated to let you soak up views of the rolling hills straight from the backyard. There’s also a fire pit with plenty of seating.
Best location: Private Paradise
This tiny stay has only three rooms—a basic living room, bedroom, and bathroom.
Despite the limited space, it’s highly rated by guests. Part of that high rating is thanks to its location near Berkshires hot spots like Jacob’s Pillow and Tanglewood.
I think guests also appreciate the plot’s natural wonders. This cottage feels incredibly private thanks to its forest coverage. There’s also a stream that runs straight through the backyard—perfect for your Walden Pond-esque reflections.
Coziest cottage: The Sail Loft
This home dates back to 1850—which surprised me given its modern, cozy design.
What I love is that this spot doesn’t feel dated or overly formal. It feels very lived-in, which I enjoy in a more rural stay like this.
Guests are also located in the heart of the Berkshires, giving them access to plenty of activities. Along with town events, guests can explore Jiminy Peak, Mount Greylock, and Mass MoCA in just a short drive.
Most remote cottage: Off Grid Yurt
It’s not a cottage—it’s a yurt. Surprise, surprise!
While I wasn’t too taken with the visual appeal of the yurt’s exterior, this rustic stay has all the finer trappings you’d expect from a Berkshires rental. The interior is spacious, includes a kitchen, and even has a wood stove.
Best of all, it’s located in a remote forest. That means that there’s thick coverage all around the yurt, offering a truly private stay in Mother Nature.
The only catch is that the bathroom is a compost toilet—but I’d happily accept this bathroom setup in exchange for such a remote feel and unique construction.
Most historical cottage: Stone School Cottage
This historical cottage was first built back in 1832 as a schoolhouse—and it functioned as one all the way up until 1950.
Its owners have since transformed the space into a bright and open cottage. But this rental still retains original features like its cobbled stone walls, chalkboards, and hardwood floors.
The setup is a little unique, as there’s a second floor that functions like a studio apartment. But if you’re a fan of historical stays, then that’s not likely to be a problem.
Best modern cottage: The Yellow Lakefront
Don’t want to stay in a schoolhouse from the 1800s? That’s understandable.
Can I interest you in a modern lakefront cottage instead? This rental includes a private deck and kayaks right on its lake. Inside, you can find all the modern amenities you’d expect from a four-star hotel.
There’s also plenty of outdoor space that makes this rental great for Berkshires first-timers. Even the sunroom is perfect for enjoying lakeside vistas no matter the time of year.