Old Bennington Holidays
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Old Bennington Holiday
Our pick of the best Old Bennington Hotel Deals
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
The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is NZ$381 per night from 2 Nov to 3 Nov
NZ$381
2 Nov - 3 Nov
includes taxes & fees
9.6/10 Exceptional! (509 reviews)
"Lovely place with lovely people. Food is great."
Reviewed on 29 Sept 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$265 per night from 4 Nov to 5 Nov
NZ$265
4 Nov - 5 Nov
includes taxes & fees
8.6/10 Excellent! (999 reviews)
a gem
"Totally perfect for mass mocha"
Reviewed on 21 Sept 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.
What to do in Old Bennington
Vermont RT 100 Self Guided Driving Audio Tour
NZ$29
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
