The Berkshires, Massachusetts

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. For a transformative wellness experience, visit Canyon Ranch Lenox, nestled in the Santa Catalina Mountains. This historic New England estate offers an expansive fitness complex, spa, daily wellness activities, outdoor exercise opportunities, and more.

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