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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