A weekend away at one of the best Berkshires hotels or rental homes is the perfect year-round escape for scenic mountain views and historic charm, whether you choose to bunk at a bucolic inn or an Airbnb from the 1800s that comes blessed with a moody, Wes Anderson-esque design scheme.
Concentrated in western Massachusetts and parts of Connecticut, plus less than a three-hour drive from New York City, the region boasts hiking trails just as incredible as its antiquing scene, making it the ideal weekend departure for any kind of traveler in the tri-state area and even further afield. Think fireplaces, darling B&Bs, and of course, many creature comforts.
If you’re in the mood for an outdoors-focused weekend, stay close to Great Barrington, where ski culture rules all year round, or base yourself in a town like Lanesborough or Hancock, near Mount Greylock. Fans of the History Channel will love a stay in Stockbridge, where a picturesque small town highlights the history of the mountainous region. And those looking to indulge in all things culture need look no further than Tanglewood and Jacob’s Pillow.
Take a more personality-based approach to booking your time in the Berkshires by considering the kind of home away from home you’re after. Cozy cottage with some Victorian flair? Photo-ready luxury hotel? Options abound in this often-overlooked stretch of glorious mountains and hidden New England gems. Read on for the best hotels and rentals we highly recommend for your next trip.
Berkshires Hotels
Perks: Pet-friendly, 20 acres of grounds to explore, working fireplaces, breakfast included
Set upon a 20-acre bucolic hillside property, this restored Georgian-Federalist residence transports you to yesteryear—to 1792 to be exact. The owners of the country estate have remained faithful to its history, refurbishing the nine fireplaces (yes, you read that right: nine!) and furnishing it with antiques. No need to worry about the vintage style translating to dated amenities though—modern touches such as radiant-heat bathroom floors ensure present-day comfort. An added bonus? You can bring your fur babies, as the bed and breakfast is pet-friendly. From $425 per night.
Perks: Located near historical landmarks and plenty of hiking trailheads, free breakfast and daily happy hour, with only eight guest rooms
Boutique-hotel style meets B&B warmth at this new spot from designer Annie Selke. With free breakfast, a happy hour, and only eight rooms, this is the perfect spot for design lovers who want to mix and mingle with other guests. Located in Lenox, its colonial landmarks as well as many miles of trails and hiking paths are perfect for hikers and history buffs alike. From $524 per night.
Perks: Working fireplaces, on-site restaurant and bar, 24-hour concierge
Fireplace? Check. Library? Check. Gorgeous chairs you’ll want to throw in your trunk and take home? Also check. A “writer's mountain retreat,” this 1970s lodge underwent major renovations recently, preserving just the right amount of original ’70s flair in the updated design. Replete with a vibey cocktail bar and restaurant for sit-down meals, the hotel also offers grab-and-go options for visitors who want to take advantage of their curated experiences or venture out on their own. From $178 per night.
Perks: Wellness-focused amenities like a fitness center and spa, on-site cooking classes, and all-inclusive options for those who want to immerse themselves in the area
Opulent, experiential, and on the pricier side, Canyon Ranch is an upscale wellness retreat housed in a stunning 19th-century mansion. Offering a wide variety of fitness classes, spa services, healthy cooking classes, an indoor and outdoor pool, and a ropes course, this hotel is perfect for those who are looking for a holistic wellness experience that doesn’t skimp on luxury. From $1,500 per night.
Perks: Each room has a unique design, is pet-friendly, saltwater swimming pool, and private cabins coming in 2026
There’s a thin line between overly curated and impeccably arranged. Tourists, a hotel with a sizable social following, sits staunchly on the side of great arrangements. A restaurant in the hotel worth the trip, unique guest rooms in muted palettes, and a compelling list of on-site activities, make this the perfect spot for the traveler in the mood to get social. Plus, it’s dog-friendly for those traveling with canine companions. From $249 per night.
Perks: Located at the Massachusetts Museum of Contemporary Art, on-site performances through Studio 9, swimming pool, sauna, and hot tub, breakfast included in your stay
Those looking to experience small-town living in the Berkshires should stay at The Porches Inn, located in North Adams. The hotel itself features distinctive, color-coded designs in every room, which were converted from 19th-century mill workers’ cottages. Sojourning at this hotel allows you to immerse yourself in the local arts scene as you’re posted right by the Massachusetts Museum of Contemporary Art (MASS MoCA) with its excellent programming: Sol Lewitt murals and exhibitions from the likes of James Turrell and Laurie Anderson. When you’re done taking in all the modern art, settle in for a brewski next door at the Bright Ideas Brewery which serves all sorts of craft beers, from open tap brews to full growlers of the stuff. From $249 per night.
Perks: Gilded Age architecture, all-inclusive rates, wellness-focused activities like equine therapy, beekeeping, and spa treatments, digital device-free campus
In need of a detox? Whether it’s a physical or digital detox (or both) that you’re after, Miraval is the top choice. A stately Gilded Age mansion is at the heart of the property, which was originally landscaped by none other than Frederick Law Olmstead, but the rooms and suites have been redesigned by AD 100’s Ken Fulk with today’s modern travelers in mind. The rates are all-inclusive, with dining options that encourage mindful eating and a wide range of wellness-focused activities that include everything from equine therapy to beekeeping, not to mention Ayurvedic treatments at the 29,000-square-foot spa. From $932 per night.
Private Homes
Perks: Great for large groups, full chef’s kitchen, hot tub, sweeping mountain views
Sleek lines, a mix of dark and light woods, and floor-to-ceiling windows make for a contemporary rustic home that feels as it’s been transported from the Pacific Northwest. A huge butcher block-topped island provides a plethora of food prep space, while the open plan allows cooks to easily mingle with the rest of the guests. After dinner, take a dip in the cedar hot tub while taking in the mountain vistas. From $791 per night.
Perks: Curated interiors, outdoor space, working fireplaces, five bedrooms all with at least a queen-sized bed
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.
