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! (223 reviews)
This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again.
Reviewed on 2026/1/12
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NT$5,857 per night from Mar 1 to Mar 2
NT$5,857
NT$6,543 total
Mar 1 - Mar 2
includes taxes & fees
9.6/10 Exceptional! (571 reviews)
I had a pretty exceptional stay they accommodated my requests without issue the room was clean aside from the hair in the shower, the heating system was quite loud and that woke me up multiple times throughout the night but having a charger on site for the Tesla was a big selling point for me especially ...
Reviewed on 2026/1/26
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is NT$3,961 per night from Feb 24 to Feb 25
NT$3,961
NT$4,425 total
Feb 24 - Feb 25
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Nice location and beautiful lobby.
Reviewed on 2026/1/27
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.
Prospect Mountain Cross-Country Ski Center
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.
Bennington Museum
You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
