Old Bennington Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundable
The price is ￥21,703 per night from Nov 6 to Nov 7
￥21,703
￥24,242 total
Nov 6 - Nov 7
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Kind staff!
Reviewed on Oct 28, 2025
The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is ￥30,048 per night from Nov 17 to Nov 18
￥30,048
￥33,564 total
Nov 17 - Nov 18
includes taxes & fees
9.6/10 Exceptional! (532 reviews)
Didn’t have the breakfast. Only drawback was the beds. Mattresses made our backs hurt.
Reviewed on Oct 31, 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.
Discover the most popular places to visit in Old Bennington
Bennington Battle Monument
Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Bennington Potters Yard
You can do some window-shopping at Bennington Potters Yard during your stay in Bennington. Discover the coffeehouses and its art scene while you're in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
