Old Bennington Packages (Flight + Hotel)
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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
The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is ฿6,436 per night from 23 Nov to 24 Nov
฿6,436
฿7,189 total
23 Nov - 24 Nov
includes taxes & fees
9.6/10 Exceptional! (528 reviews)
We loved staying in Williams Inn! The property was beautiful, the lobby fireplace a warm welcome from the frigid trip that took us there, and our room was very nice! The Barn restaurant had great food and drinks and I enjoyed being in the company of so many Williams College students and professors/parents.i ...
Reviewed on 20 Oct 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,106 per night from 26 Nov to 27 Nov
฿5,106
฿5,703 total
26 Nov - 27 Nov
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Good value. A good place.
Reviewed on 24 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.
What to do in Old Bennington
Vermont RT 100 Self Guided Driving Audio Tour
฿555
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
