Old Bennington
Travel Guide
Visit Old Bennington
The Four Chimneys Inn
This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was ...
Reviewed on 2 Sept 2025
Hotel Downstreet, an Ascend Collection Hotel
Staff was pleasant and helpful, room spacey and all immaculate .
Reviewed on 11 Jan 2026
The Williams Inn
Accommodating staff!
Reviewed on 14 Jan 2026
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Amazing location, walk out to lift in backyard!
Reviewed on 3 Jan 2026
Crafts Inn, Hotel Suite with pool and hot tub.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
The cabin is wonderful. And as incredible as it sounds, it's much more beautiful and impressive in person. Surrounded by nature. Very peaceful and quiet. I recommend going for at least 3 days. You'll thank me later. And as a final piece of advice, since it's such a small town, I recommend doing your ...
Reviewed on 3 Dec 2025
Popular places to visit
Bennington Battle Monument
Learn about the local history of Old Bennington with a stop at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Old First Congregational Church
Find out about the history of Old Bennington when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.
Prospect Mountain Cross-Country Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.
Prospect Mountain Nordic Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and cafes.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
You can spend an afternoon exploring the galleries in Hemmings Motor News Car Lover's Convenience Store & Vehicle Display during your travels in Bennington. While you're here, you can savour the cosy cafes.
Bennington Museum
You can spend an afternoon exploring the galleries in Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and cafes.
