The 30 Best Luxury lodging in Bennington, Vermont

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.

Eddington House Inn is a charming lodging establishment located at 21 Main Street in Vermont, United States. This historic inn offers a cozy and welcoming atmosphere for guests looking to experience the beauty and charm of New England. With comfortable accommodations, delicious breakfast options, and friendly staff, Eddington House Inn is the perfect destination for a relaxing getaway in the heart of Vermont. Whether you're visiting for a romantic weekend, a family vacation, or a solo retreat, Eddington House Inn is sure to provide a memorable and enjoyable stay.

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.

Paradise Inn, located at 141 Main Street in Bennington, Vermont, is perhaps the best hotel in the area according to Frommer's Travel Guide. This family-owned inn offers a peaceful and relaxing atmosphere surrounded by beautiful gardens and lawns, just a short walk from downtown Bennington. With 77 spacious rooms offering a variety of amenities such as in-room saunas, balconies, and patios, Paradise Inn is the perfect lodging choice for a weekend getaway or as a base for exploring Southern Vermont. Free WiFi is available throughout the inn, and complimentary coffee is provided in the lobby.

Located in the charming town of Bennington, Vermont, the Starlight Inn offers a cozy and comfortable lodging experience for travelers seeking a peaceful retreat. Situated at 357 U.S. 7, this quaint inn provides a warm and welcoming atmosphere, perfect for relaxing after a day of exploring the beautiful surroundings. With its convenient location and friendly staff, the Starlight Inn is the ideal choice for those looking for a relaxing stay in Vermont.

Monument View Apartments offers comfortable and spacious lodging in Bennington, Vermont. Located at 51 Hilltop Drive, this institution provides stunning views of the surrounding monuments and landscapes. The apartments are well-equipped with modern amenities and are perfect for both short and long-term stays. Whether you are visiting for business or pleasure, Monument View Apartments offers a convenient and relaxing accommodation option in the heart of Bennington.