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
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 2 Sept 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is 3.285.676 ₫ per night from 2 Feb to 3 Feb
3.285.676 ₫
3.670.099 ₫ total
2 Feb - 3 Feb
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Staff was pleasant and helpful, room spacey and all immaculate .
Reviewed on 11 Jan 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is 4.891.464 ₫ per night from 25 Jan to 26 Jan
4.891.464 ₫
5.463.765 ₫ total
25 Jan - 26 Jan
includes taxes & fees
9.6/10 Exceptional! (560 reviews)
General ambience is lovely.
Reviewed on 8 Jan 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.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
You can spend an afternoon exploring the galleries in Hemmings Motor News Car Lover's Convenience Store & Vehicle Display during your travels in Bennington. While you're here, you can savour the cosy cafes.
