The Berkshires are one of the country’s most memorable escapes thanks to their supercharged list of attractive offers.
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Do you like history? The Berkshires are home to historic towns like Lenox and Sheffield, founded before the formation of the United States.
What about scenic views of nature? The Berkshires are within the Green Mountain range and are home to parts of the Appalachian Trail and Massachusetts ’ highest peak, Mount Greylock. (Just watch out for ticks.)
Or do you prefer arts and culture? The Berkshires are home to art festivals, galleries, studios, exhibits, and more, which you can experience in the area’s many public venues and events.
I have just one tip if you’re eager to visit the Berkshires: Book your adventure during the fall season. The Berkshires are home to mature woodlands that come alive with fall foliage displays—and they’re some of the best in the country. Expect vibrant colors through September and October.
If you want to maximize your autumn immersion, book one of these cottage Airbnbs in the Berkshires. They’ve got space to roam and appreciate the views.
Most scenic cottage Airbnbs in the Berkshires to enjoy this autumn: at a glance
- Best for hikers: Artist’s House
- A modern cottage: Granite Ledge
- Most central location: Carriage House
- Best historic stay: The Gardener’s Cottage at Ventfort Hall
- Best for large groups: Chase Hill
- A quiet, casual getaway: The Cobble Barn
- For water-lovers: Rustic Pond Cabin
- Best for staying within your budget: Historic Schoolhouse
- Best for disappearing in nature: Zen Cottage
- Best cottage-core vibes: Rustic Farmhouse
- Best for history and culture seekers: Belle Meade
Cottage Airbnbs in the Berkshires for a flawless fall escape
Artist’s House (Sheffield)
If you’re heading to the Berkshires to be swept away by nature as the fall leaves change colors, this three-bedroom home gives you an excellent hideaway. First, the home is surrounded by trees on five private acres. Trails to Mount Washington State Park can be found right outside the home. As a perk, you’re also in Sheffield, one of the cutest small towns in the region.
Granite Ledge (Great Barrington)
As you’ll see below, most of the cottage Airbnbs in the Berkshires deliver on old-school charm and character. If you prefer to stick to a more modernized layout, this cabin is for you. It’s a three-bedroom located in Great Barrington, another charm-packed small town. On the property, you can also enjoy the granite bluff and mature woodlands, which come alive each autumn. Inside, you’ll be treated to a modern, hygge-style setup that’s bright and clean.
Carriage House (Great Barrington)
There are many reasons to love this two-bedroom historic carriage house. It’s been beautifully renovated to maintain its wood details, then refurbished with modern appliances and features. The yard is also very lush, with mature trees and a small garden. But the real coup is its location in Great Barrington. You’re just a short drive to its top galleries, restaurants, and more. The rest of the Berkshires top sites are within reach from this central hub, too.
The Gardener’s Cottage at Ventfort Hall (Lenox)
This austere, historic Airbnb is located on the grounds of the Gilded Age-era Ventfort Hall, built in 1893 for JP Morgan’s sister. There is a fantastic balance of old and new. For example, the claw-foot bathtub is in a bathroom with radiant heat flooring. As a perk, when you rent this two-bedroom Airbnb, you also get four complimentary tickets to the Mansion at Ventfort Hall, located nearby in Lenox.
Chase Hill (North Adams)
There’s a little bit of everything at this unique four-bedroom cottage. First, you’ve got space to fit eight guests with four bedrooms and a sleeper sofa. Second, you’re located in the heart of North Adams, a scenic historic town that’s home to the famous MoCA. Third, the rental gives you access to the property’s scenic fire pit and Finnish sauna.
The Cobble Barn (Canaan)
Looking to slip off the map for a while? Head to the two-bedroom Cobble Barn in Canaan. It’s tucked away in the Connecticut portion of the Berkshires, which are even quieter. This home gets its name from Cobble Mountain because of its location at the base, putting you close to hiking trails and Lime Rock Park. Lastly, this converted barn has rustic features that are warm and welcoming.
Rustic Pond Cabin (Colebrook)
I have two Colebrook Airbnbs on this list (including Rustic Farmhouse, below), which is technically located just outside the Berkshires. The adjacent town of Litchfield Hills is considered the border town—but I’ll let you decide if this rental is worth staying outside the official Berkshires zone.
The main appeal is its location on a quiet, private pond. You’ve got kayaks, a sandy beach, and a fire pit to enjoy, letting you soak up the wonders of autumn with total privacy. The cabin itself is a bit rustic, but has all the features you could want—from a full kitchen to attic rooms with skylights. The wood interior is also a treat for those who like classic cabin getaways.
Historic Schoolhouse (Falls Village)
It’s hard to find Airbnbs in the Berkshires that don’t cost an arm and a leg. This historic cottage in Canaan comes pretty close to staying in budget, especially if you fill both bedrooms. It’s perfect for those who enjoy historic features, too, as this home has its original wood-burning stove and wood-paneled ceilings. The original schoolhouse dates back to the 1800s, giving you a centuries-old cottage to hang your hat.
Zen Cottage (Great Barrington)
One look at the photos of this three-bedroom rental will already have you relaxing. This gorgeous zen palace comes with plenty of space both inside and outside on the remote, forested grounds. And while the term ‘zen’ might make you imagine minimalism, the cottage is actually rich with organic materials and bright textiles that offer a cozy stay.
Rustic Farmhouse (Colebrook)
As with the Rustic Pond Cabin (above), this rental is outside the Berkshires by a few minutes, located in Colebrook, Connecticut. In exchange for the distance to towns like North Adams and Sheffield, you’ll get yet another cottage-core-worthy rental. The interior is decked out with wood features, along with a blend of modern furniture and antiques. The screened porch is also a treat, along with the hot tub out back. This three-bedroom home is also located close to Litchfield Hills, too, letting you take on autumn adventures like brewery-hopping.
Belle Meade (Sheffield)
Let’s say you want to visit the Berkshires during autumn to enjoy the season… but what you’re really after is a dose of arts and culture. This two-bedroom Sheffield home puts you close to the region’s top cultural venues, along with historic sites like the Sheffield Plain Historic District. Tanglewood and Jacob’s Pillow are also a short drive away—and the drive there is a gorgeous country road, to boot. Culture and history aside, the backyard setup, which includes a dining table, is also very charming.
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