TOP 30 Unique and charming inn in Bennington, Vermont

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Four Chimneys Inn & Restaurant is a charming Vermont B&B located at 21 West Road in Bennington, United States. Offering an intimate yet grand feel reminiscent of graceful summer homes of the past, our uniquely appointed guest rooms maintain old-world details while providing modern amenities for a comfortable stay. Whether you're looking for a romantic getaway, a sister weekend, or accommodations for business travel, Four Chimneys Inn is the perfect choice. Our inn provides a magical respite from the day-to-day frenzy, making it a longstanding favorite lodging choice for Bennington College families and business travelers alike. With modern amenities and a welcoming atmosphere, it's no wonder that many area HR departments entrust their visiting business travelers and VIPs to our care. Additionally, we now offer an EV charger for our overnight guests, ensuring worry-free travel for those with electric vehicles.

SOUTH SHIRE, a Little Hotel, is a charming lodging located at 124 Elm Street in Bennington, Vermont, United States. This institution celebrates the romance of the Gilded Age in Southern Vermont, offering guests a unique and intimate experience. Originally built as the private residence of Louis A. Graves and designed by the renowned architect William C. Bull, the South Shire Inn boasts stunning Victorian architecture that reflects the grandeur of the era. With ten-foot ceilings, a mahogany-paneled library, ornate fireplaces, leaded glass pocket doors, and raised plaster moldings, this hotel is a true gem in the Shires of Vermont.