This five-bedroom Italianate house makes for an elegant home base for fall gatherings with friends, with ample room to spread out. Built in the 1850s as a church rectory, the house has since been given a contemporary facelift with color-drenched rooms, a marble and steel chef’s kitchen, and modern furnishings—all of which work well with the original carpentry, wood-burning fireplace, and soaring, 13-foot ceilings.
A quick five-minute walk brings you right into the charming town of West Stockbridge. The postage stamp sized-town is brimming with cafés and shops; including the historic Baldwin Extracts, which for over a century has been a draw for in-the know chefs and bakers. A short drive away, Stockbridge offers a quintessential Berkshires experience with its storied Red Lion Inn, the Norman Rockwell Museum, and Naumkeag, a public garden and historic home that’s one of the area’s most splendid examples of Gilded Age architecture. (Expect an opulent pumpkin display if you’re visiting aroung Halloween.)
Rooms: 5 bedrooms, 4 bathrooms
Amenities: Wood burning fireplace, AC, Bluetooth sound system, BBQ, fire pit
Location: West Stockbridge, Massachusetts
Best For: A stylish friend group trip.
Courtesy of the Airbnb photographer community
MASS MoCA, the sprawling contemporary art museum occupying 24 acres of the former Arnold Print Works factory complex, is practically your neighbor when you stay at this mid-century home. You could easily spend an entire stay wandering through the galleries, but the house itself makes a compelling case for lingering in place, with its sunroom, fireplace, and record player made for enjoying long fall evenings.
Just down the road, Natural Bridge State Park offers an abundance of trails for the outdoorsy traveler, while The Clark—about twenty minutes away in the college town of Williamstown—provides another cultural counterpoint, with its celebrated collection of Impressionist art and expansive, sculpture-filled grounds.
Rooms: 3 bedrooms, 1.5 bathrooms
Amenities: Fireplace, record player
Location: North Adams, Massachusetts
Best For: Museum aficionados who could spend the entire trip gallery-hopping.
Courtesy of the Airbnb photographer community
