Old Bennington Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Emily Whalen
Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is 6.230.017 ₫ per night from 28 Apr to 29 Apr
6.230.017 ₫
6.790.718 ₫ total
28 Apr - 29 Apr
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is 3.748.424 ₫ per night from 14 May to 15 May
3.748.424 ₫
4.186.991 ₫ total
14 May - 15 May
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Nice staff comfy bed nice views
Reviewed on 8 Apr 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is 8.138.442 ₫ per night from 28 Apr to 29 Apr
8.138.442 ₫
9.090.639 ₫ total
28 Apr - 29 Apr
includes taxes & fees
9.6/10 Exceptional! (616 reviews)
Clean room
Reviewed on 17 Apr 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
Learn about the local history of Old Bennington with a stop 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 when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.
Bennington Potters Yard
You can do some window-shopping at Bennington Potters Yard during your trip to Bennington. Discover the cafes and its art scene while you're in the area.
