Old Bennington Trip
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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 ₹17,316 per night from 17 Nov to 18 Nov
₹17,316
₹19,342 total
17 Nov - 18 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 ₹13,729 per night from 25 Nov to 26 Nov
₹13,729
₹15,335 total
25 Nov - 26 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.
Popular places to visit
Bennington Battle Monument
4/5(3 reviews)
Learn about the local history of Old Bennington with a stop at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Prospect Mountain Nordic Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and cafes.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
