Old Bennington Holidays
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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
The price is €126 per night from 13 Nov to 14 Nov
€126
13 Nov - 14 Nov
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
Reviewed on 9 Oct 2025
The Williams Inn
101 Spring Street, Williamstown, MA
The price is €204 per night from 2 Nov to 3 Nov
€204
2 Nov - 3 Nov
includes taxes & fees
9.6/10 Exceptional! (520 reviews)
"Lovely clean room with a fabulous shower. Tea/coffee available 24 hours with a choice of milks which is great. Refillable glass bottle in the room to collect fresh water which meant no plastic bottles. Plenty of parking, cosy lobby and restaurant food excellent."
Reviewed on 10 Oct 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
