Old Bennington, VT
Travel Guide





Visit Old Bennington

The Four Chimneys Inn
This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again.
Reviewed on 2026/1/12

The Williams Inn
I had a pretty exceptional stay they accommodated my requests without issue the room was clean aside from the hair in the shower, the heating system was quite loud and that woke me up multiple times throughout the night but having a charger on site for the Tesla was a big selling point for me especially ...
Reviewed on 2026/1/26

Hotel Downstreet, an Ascend Collection Hotel
Nice location and beautiful lobby.
Reviewed on 2026/1/27

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
Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained
Reviewed on 2026/1/31
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.
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.
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.
Woodford State Park
You can take time to visit Woodford State Park during your travels to Woodford.
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
- Bennington College
- Williamstown Theatre Festival
- Sugar Shack
- Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
- Williams College Museum of Art
- Grafton Lakes State Park
- Bennington Battlefield Historic Site

