Channel your inner Wes Anderson with a stay at this impossibly charming home filled with thoughtful details and design choices. The adjoining garden takes the charm factor through the roof. A renovated 19th-century rectory, we’ve already dubbed it “the coolest Airbnb in Massachusetts” for a reason. The Norman Rockwell Museum also resides in Stockbridge for a fun day activity. From $1,384 per night.
Perks: Unique architecture, expansive outdoor space, close to ski slopes, working fireplace
Whether you’re visiting the Berkshires in the summer for a concert at Tanglewood, during the fall for leaf-peeping or in the winter to hit the slopes, the wrap-around windows of this midcentury-inspired cabin provide stunning views. After a day on the mountains, skiers can return to enjoy the cozy fireplace underneath the vaulted ceilings, while the expansive deck provides a place to grill, eat, or lounge while surrounded by the forest. Think of it as luxury living, just in a treehouse. From $535 per night.
Perks: Unique architecture, ideal for large groups, chef’s kitchen, sauna, large deck with grill
Tucked away in the small town of Mill River, you’ll find a renovated church, circa 1892, ideal for group getaways. The three bedroom, three bathroom rental property offers 4,000 square feet of unique entertaining space, towering ceilings, and stained-glass windows to enjoy—the original altar is even still in place. With an outdoor sauna, chef’s kitchen, and game room, this home houses up to 10 guests comfortably (no pull-out couch or air mattresses needed here) for a weekend in the hills. From $1,540 per night.
Perks: Tucked away from main roads, plenty of outdoor areas to explore, working fireplace, close to Berkshires trails and towns
With architecture that looks like something out of a fairy tale, this adorable Tudor-style home boasts a signature thatched roof and turret. Two bedrooms and two bathrooms comfortably sleep four, but the real magic is in the surrounding gardens and fields. Set on four acres, the rental home is tucked away from the main roads for a quiet, disconnected stay. The ponds and trails provide ample space to wander. Inside, wood paneling and bohemian decor offer a different take on the cabin aesthetic with plenty of woven textures and bed canopies. From $797 per night.
Perks: Expansive views, newly renovated kitchen, three-season porch, 75-acres of land
Situated on 75-acres of hiking trails, fields, and streams to explore, this quaint cabin is great for the adventurers. If you plan to cozy up indoors, you’ll still get views of the rolling hills from the screened-in porch. This two-bedroom home comfortably sleeps four, while a sleeper sofa allows for up to six guests. With a freshly renovated kitchen and bathroom, along with expansive outdoor entertaining space, the cottagecore-leaning interiors offer everything you may need for a refreshing Berkshires stay. From $970 per night.
Craving an escape? From colorful carry-ons to cleverly designed packing cubes (how did we ever travel without them?), shop everything you need to make the journey in style—and as streamlined and stress-free as possible.
