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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.
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Berkshires Hotels | Private Homes
Berkshires Hotels
City: Richmond, Massachusetts
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.
City: Stockbridge, Massachusetts
This quaint country inn has been a fixture on Main Street in Stockbridge since 1773. Filled with antiques and decorated with dainty wallpaper, it’s positively dripping in New England charm. But that doesn’t mean modern comforts are lacking. Aside from free parking, there’s a fitness center, a heated outdoor pool, hot tub, and free Wi-Fi. There are also several dining options on-site, from the elegant main dining room to the Lion’s Den speakeasy that hosts live music. From $222 per night.
City: Lenox, Massachusetts
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 $796 per night.
City: Lenox, Massachusetts
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 $141 per night.
City: Lenox, Massachusetts
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 $1,000 per night.
City: North Adams, Massachusetts
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.
City: North Adams, Massachusetts
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 $278 per night.
City: Lenox, Massachusetts
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 $899 per night.
Private Homes
City: East Nassau, New York
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 $578 per night.
City: West Stockbridge, Massachusetts
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 $1,050 per night.
City: Otis, Massachusetts
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 $348 per night.
City: Dalton, Massachusetts
A tavern/stagecoach stop in the 1800s, this renovated gem is centrally located within the Berkshires. Cozy nooks dot the mostly black-and-white space. The outdoor deck, which is fully furnished, is great for entertaining outdoors. With six bedrooms, you better start sending out invites. From $500 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.
