Old Bennington Holidays
Photo by Emily Whalen
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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 €120 per night from 2 Feb to 3 Feb
€120
2 Feb - 3 Feb
includes taxes & fees
8.6/10 Excellent! (1,000 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 €179 per night from 29 Jan to 30 Jan
€179
29 Jan - 30 Jan
includes taxes & fees
9.6/10 Exceptional! (561 reviews)
Accommodating staff!
Reviewed on 14 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
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.
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