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Discover western Massachusetts’ most revered vacation destination, The Berkshires, with Inspirato. Set amid the region’s rolling hills and dense forests, Woodland Estate is a quintessential Berkshires getaway set on 72 private and scenic acres. The mountain lodge-style home boasts a heated outdoor pool, hot tub, and fire pit, as well 180-degree views of Mount Greylock—all just a few minutes’ drive from Williams College and 25 minutes from skiing and hiking at Jiminy Peak Mountain Resort.
In the Berkshires of southwestern Massachusetts, six-bedroom Sunset Falls is a modern and inviting home with abundant outdoor living space, a hot tub, beer garden, and fire pit. Skiing and hiking at Butternut Ski Area are just a 15-minute drive away
Tucked in snug between the Taconic and Hoosac mountain ranges in western Massachusetts and Connecticut, the Berkshires have long been a popular vacation destination, particularly for well-heeled East Coasters in search of a nearby mountain escape. Today, the Berkshires still draw in tourists with a wealth of natural beauty and ever-appealing quaint towns that stud the pastoral landscape—places like Williamstown, Lenox, and Stockbridge. The region has historically served as inspiration for artists, including writers like Herman Melville and Edith Wharton; that same prominent artistic streak can still be found today in the region’s many galleries, theaters, and museums.
Tanglewood is the Berkshires’ premier outdoor summer concert series, a tradition that began in 1936 when the Boston Symphony Orchestra first performed here. Today’s lineup is often a mix of classical musicians, folk singers, and even the occasional pop star.
A small-town art museum with big-city wares, the Clark houses Impressionist masterpieces from heavy hitters like Renoir, Degas, and Rodin. Also of note is its collection of 18th-century furniture and fine porcelain.
Earn your bragging rights in this state park, where you can hike part of the Appalachian Trail or choose to summit Mount Greylock, the highest peak in the state at 3,491 feet.
Towns in the Berkshires typically experience all four seasons. Summers are warm and wet, with highs in the mid-70s. Fall brings gorgeous foliage and brisker weather. Winters are cold, dry, and often snowy, with temperatures frequently dipping into the teens and 20s.