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Discover safe, luxurious vacations with Inspirato. Create your free account to see all of our destinations and accommodations within the Inspirato Collection.
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.
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.