Old Bennington Holidays
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Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is 6.724.287 ₫ per night from 10 Jun to 11 Jun
6.724.287 ₫
7.329.472 ₫ total
10 Jun - 11 Jun
includes taxes & fees
9.4/10 Exceptional! (284 reviews)
"Had a great experience here. The staff was friendly and helpful. Chatting with the bartender and other guests at the bar over a nightcap made for an enjoyable evening. The room was clean and comfortable and the breakfast was fantastic."
Reviewed on 26 May 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is 4.287.102 ₫ per night from 8 Jun to 9 Jun
4.287.102 ₫
4.788.692 ₫ total
8 Jun - 9 Jun
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Check in was simple and quick. Staff was courteous and helpful. The room was clean and spacious. We had a pleasant stay and checkout was simple."
Reviewed on 1 Jun 2026
The Williams Inn
101 Spring Street Williamstown MA
The price is 8.658.951 ₫ per night from 15 Jun to 16 Jun
8.658.951 ₫
9.672.048 ₫ total
15 Jun - 16 Jun
includes taxes & fees
9.6/10 Exceptional! (631 reviews)
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."
Reviewed on 30 May 2026
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.
Popular places to visit
Bennington Battle Monument
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.
Bennington Center for the Arts
Enjoy an outing to Bennington Center for the Arts during your stay in Bennington. Experience the area's art scene and museums.
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.
