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 2025/9/2
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is NT$3,622 per night from Dec 20 to Dec 21
NT$3,622
NT$4,046 total
Dec 20 - Dec 21
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
I don’t have a single complaint about this hotel! Everything was perfect! Staff was great, parking was easy, everything was clean! My family and I will definitely be staying here again in the future!
Reviewed on 2025/12/5
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NT$6,149 per night from Dec 14 to Dec 15
NT$6,149
NT$6,868 total
Dec 14 - Dec 15
includes taxes & fees
9.6/10 Exceptional! (548 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.
Reviewed on 2025/12/7
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
4.5/5(71 reviews)
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.
Prospect Mountain Cross-Country Ski Center
4.5/5(11 reviews)
Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
4.5/5(2 reviews)
You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
