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 Sep 2, 2025
Hotel Downstreet, an Ascend Collection Hotel
Staff was pleasant and helpful, room spacey and all immaculate .
Reviewed on Jan 11, 2026
The Williams Inn
Accommodating staff!
Reviewed on Jan 14, 2026
Bennington Gem w/ Smart TV Near Historic District!
Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 ...
Reviewed on Oct 21, 2025
Breathtaking Mtn Views: Stylish Rustic Retreat!
Long Trail House at Stratton Mountain Resort
Nice lodge. Room needs updating
Reviewed on Oct 19, 2025
Popular places to visit
Bennington Battle Monument
Learn about the local history of Old Bennington when you spend time 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 with a stop 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 coffeehouses.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.
Bennington Museum
You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.
Things to do
Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway
