Old Bennington, VT
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 2025/9/2
Hotel Downstreet, an Ascend Collection Hotel
I don’t have a single complaint about this hotel! Everything was perfect! Staff was great, parking was easy, everything was clean! My family and I will definitely be staying here again in the future!
Reviewed on 2025/12/5
The Williams Inn
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.
Reviewed on 2025/12/7
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 2025/10/21
Breathtaking Mtn Views: Stylish Rustic Retreat!
Long Trail House at Stratton Mountain Resort
Nice lodge. Room needs updating
Reviewed on 2025/10/19
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.
- Bennington Battle Monument
- Bennington Museum
- Massachusetts Museum of Contemporary Art
- The Clark Art Institute
- Mount Snow Golf Course
- Prospect Mountain Cross-Country Ski Center
- Sugar Shack
- Bennington College
- Williamstown Theatre Festival
- Grafton Lakes State Park
- Williams College Museum of Art
- Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
- Windsor Lake Park