
Old Bennington Vacation Packages
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Your Old Bennington Vacation
The rich history and spectacular views are just the start of the things Old Bennington has on offer. Experience the very best of this interesting city the way you want with a personalized Old Bennington vacation package. If your trip to Old Bennington includes a little sightseeing, check out famous attractions like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Expedia will help you escape the everyday. Tailor your vacation to Old Bennington to suit your travel style, whatever that may look like.
Old Bennington Hotel Deals

The Four Chimneys Inn
21 West Road Bennington VT
The price is CA $358 per night from Aug 4 to Aug 5
CA $358
CA $391 total
Aug 4 - Aug 5
includes taxes & fees
9.4/10 Exceptional! (290 reviews)
"Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar"
Reviewed on Jul 24, 2026

Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 31 to Sep 1
CA $139
CA $152 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"Pool offered. Out of service. Breakfast offered None!!!!!!"
Reviewed on Aug 2, 2026

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $223 per night from Sep 1 to Sep 2
CA $223
CA $249 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Room was clean and staff was nice. Air conditioner was a little noisy"
Reviewed on Aug 1, 2026
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.
Stay near popular Old Bennington attractions
What to do in Old Bennington

Vermont RT 100 App-Guided Driving Audio Tour
CA $24
per traveller
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







