Old Bennington Vacations

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Old Bennington Hotel Deals

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
9.6/10 Exceptional! (222 reviews)
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

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The Four Chimneys Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is ￥19,344 per night from Jan 27 to Jan 28
￥19,344
￥21,607 total
Jan 27 - Jan 28, 2026
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Courteous staff

Reviewed on Dec 19, 2025

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is ￥30,435 per night from Jan 13 to Jan 14
￥30,435
￥33,996 total
Jan 13 - Jan 14, 2026
includes taxes & fees
9.6/10 Exceptional! (555 reviews)
Great staff, great rooms, we had a little issue with the door not opening, but they were quick to fix it. Bar staff, fantastic! Restaurant (we had brunch) delicious. This is our go to hotel when we stay in the Berkshires

Reviewed on Dec 28, 2025

The Williams Inn
See all 996 properties in Old Bennington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Old Bennington

Bennington Battle Monument showing landscape views

Bennington Battle Monument

4.5/5(71 reviews)

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.

Bennington Battle Monument

Bennington Potters Yard

5/5(6 reviews)

You can do some window-shopping at Bennington Potters Yard during your stay in Bennington. Discover the coffeehouses and its art scene while you're in the area.

Bennington Potters Yard

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