Historic 9-BR Berkshires Estate Retreat

Step into timeless New England charm at The Dewey, a historic 9-bedroom, 9.5-bath estate in the heart of Lenox. Blending 18th-century character with modern comforts, this inviting retreat offers space for up to 24 guests, perfect for gatherings, celebrations, or a restorative escape in the Berkshires. The space Welcome to The Dewey, built in 1767, this storied property is where colonial craftsmanship meets contemporary comfort, creating a home designed for connection and relaxation. The estate spans 9 well-appointed bedrooms across the main house and a beautifully restored carriage house, each with curated decor, plush bedding, and thoughtful details that honor its history. Multiple gathering spaces, including a grand living room, cozy parlor, elegant dining room, and library, offer plenty of room to come together, while peaceful nooks and private suites ensure every guest can enjoy quiet retreat. Outdoors, mature gardens, stone walls, and shaded lawns set a serene backdrop for time spent together. Whether you’re preparing a shared meal in the kitchen, or heading out to explore Lenox’s cultural life, The Dewey provides an elevated home base for your Berkshires stay. Guest access Accessible with lock box Other things to note Notes & Disclaimers: Wildlife: This is a home in a rural part of the country. You may see wildlife including deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash. Weather: In the winter, there will be snow, ice, and occasional snowstorms. We recommend driving a vehicle with AWD or 4WD. Please drive with caution and be prepared with regards to the ability of your vehicle to drive in the snow. Power & Internet: This is a rural part of the country. You may lose power or internet during inclement weather. We do not issue refunds for loss of power or internet out of our control. Pets: We’re happy to welcome your pup to the home. There’s a $150 fee + tax for the first dog and $50 + tax for each additional one. If you’re planning to bring more than one, please reach out to us before completing your booking so we can get everything set up for you. For everyone’s comfort, we kindly ask that dogs stay leashed outdoors and that you clean up after them. Please note that cats aren’t permitted due to allergy concerns. Any pet-related damages may result in additional charges. Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler’s insurance.