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Although located in Western Massachusetts, the rolling hills of the Berkshires are perhaps best known as a remote hub for summering New Yorkers, beyond the Catskills, Hudson Valley, and Montauk. Home to international dance destination Jacob’s Pillow, MASS MoCA, Boston Symphony Orchestra's summer home Tanglewood, and more, the area is rich in artistic culture, lovely landscapes, decent skiing, and some pretty solid bouldering, too.
Somewhere between a Hamptons-esque escape and a remote New England outpost, the Berkshires provide a spectrum of accommodations, from rustic cabins and charming cottages to mid-century modern homes, with many vacation rentals, of course. As the Berkshires is a fairly small region, main attractions can be reached within an easy drive of all our top picks for the area’s best cabins, even if you’re tucked far back in the woods.
So, scape the confines of wherever you've been cooped up these past several months and book a stay for the near or far future at one of the following best Berkshires cabin rentals.
Vibe: Rustic Charmer
Built in the 1980’s, this unique cabin is full of interesting nooks and crannies. An open floor plan, lofted second floor, and plenty of windows make the space inviting, and the central wood stove assures you’ll stay warm and cozy during your stay. A new and well stocked kitchen is great for indulgent cooking and a desk area is there if you need to check in on emails. Hiking trails and a swimming pond is a short walk away for summer visits with snowshoeing and cross-country skiing trailheads located right across the street.
Vibe: Fancy fishbowl
Treehouses tend not to disappoint, and this one is no different. Completely secluded, spend a weekend washed in the colors of the season and the calming natural material-palate of this fish-bowl. With 300 degrees of windows, an open floor plan and vaulted ceilings, this unique industrial meets nature-lover aesthetic will keep you feeling comfy as can be. Upper Spectacle Pond is a walk away or make the drive to nearby ski areas and quaint New England towns.
Vibe: By the Brook Bliss
Hike down into the hollow that houses this quintessential New England cabin. Sitting alongside a flowing stream, this charmer features vaulted ceilings, skylights, a large stone fireplace, and a tasteful combo of antique and MCM furnishings. A king bed awaits in a loft, while downstairs, two quaint bedrooms could house friends or family. There’s even a clawfoot tub for those who enjoy a nice soak. And outdoors, a deck for wild life and star spotting. Butternut and Catamount Ski areas are close by, as well as the charming town of Great Barrington.
Vibe: Just Wright
Mid-Century from its head to its toes, this 1960s getaway was recently updated with a modern kitchen and bath. Characteristic of Frank Llyod Wright, the house creates thin boundaries between outdoors and in with large windows throughout and easy passage to the patio area. Indoor and outdoor fireplaces offer up cozy places to gather while its central location is perfect for exploring nearby Lenox, Tanglewood, Jacob’s Pillow and Great Barrington.
Vibe: Peace Beyond the Pond
Owned and operated by a pair of artists, the summer-specific Pondhouse certainly invokes a connection to your more creative and spiritual side. Built with Hemlock trees from the property, screens are the only thing between you and the outdoor world, so let's call it glamping. A recently installed composting toilet, outdoor kitchen sink, and shower mean most of your amenities are taken care of, but this is more of a disconnect and curl up with a good book type of place anyway. In a more remote location, there’s nearby hiking to enjoy, or the small towns of Ashfield and Shelburne Falls if you’re on the hunt for culture (or dinner).
Vibe: Bright Barn
Dating back to the 1940’s, this cabin offers a rustic elegance, with its exposed structure and barn-like feel. Suited best for warmer months, the cabin is a short walk to the shores of Stockbridge Bowl lake, where one can kayak, canoe, or hang on the beach. While one could easily spend their time hanging out on the expansive, multi-leveled deck, nearby Monument Mountain has great hiking, and local attractions like the Berkshire Botanical Gardens, Edith Wharton’s estate The Mount, and the town of Stockbridge offer-up plenty of things to sight-see.
Vibe: Barnhouse Bliss
A more modern rental, this 8-guest home mixes farmhouse, contemporary, and more modern aesthetics to create a country escape with urban loft sensibilities. Two spa-like bathrooms (hello stand-alone bathtub and rain-shower room thing), lofted area with two full-sized Murphy beds, screened in porch, double-height ceilings, spacious kitchen, and outdoor patio are the highlights here, made all the better by the surrounding trees. As always, Berkshire activities are within short drives, so it’s a great spot for a family or group trip.
Vibe: Handcrafted Home
Located on a healing sanctuary, this beautifully crafted off-grid 8’ x 10’ Tiny Home is great for the solo traveler or couple looking for some self-care. A mixture of on and off grid, you’ll have a full kitchen with gas stove, shower and composting toilet but no wifi and spotty cell-service, the perfect combo for some pure relaxation. MASS MoCA and Savoy Mountain State Forest are nearby for activities—for when the 80-square-foot tiny home starts feel like 80 square feet.
Vibe: New England Nice
For those looking to soak in some New England history, this modernized cabin built in 1875 will do the trick. Located in the heart of North Adams, this town home offers up easy access to the restaurants and attractions the town has to offer, while providing your own little oasis. Furnishing are a pleasant mix of modern cottage, Instagram-blogger, and MCM, with a spiral staircase to round it out. Pet-friendly, let your pup roam free in the fenced in backyard while you chill on the deck.
Vibe: Silo Suite Silo
Spend your stay admiring the beauty of the Berkshires landscape from your perch in this converted silo. A good fit for a solo or couple’s trip, a kitchenette, ¾ bath and bedroom equipped with a fireplace and great views provide all you need. Jiminy Peak is nearby for skiing, horseback riding is down the road and a short drive away is Mount Greylock State Reservation, home to panoramic views, sections of the Appalachian Trail and the highest point in Massachusetts.
Vibe: Craftsman Cute
This recently built craftsman style home was handcrafted by the owners, creating an inviting structure full of fine wood-working and charming corners, like the breakfast nook, sitting room, and unique soaking tub. A short distance to Tanglewood and Jacob’s Pillow, enjoy the outdoor art scene or hike sections of the Appalachian Trail a mere three miles away. In the warmer months, nearby lakes provide kayaking and fishing for water-lovers.