Old Bennington Vacations
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Find the Best Old Bennington Vacation Packages
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 Sep 2, 2025
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is ₩289,283 per night from Dec 1 to Dec 2
₩289,283
₩323,129 total
Dec 1 - Dec 2
includes taxes & fees
9.6/10 Exceptional! (544 reviews)
Bb
Reviewed on Nov 17, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is ₩157,191 per night from Dec 20 to Dec 21
₩157,191
₩175,582 total
Dec 20 - Dec 21
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
Wonderful Experience
Reviewed on Nov 23, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
