
Old Bennington Holidays
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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 S$285 per night from 1 Dec to 2 Dec
S$285
1 Dec - 2 Dec
includes taxes & fees
9.6/10 Exceptional! (544 reviews)
Bb
Reviewed on 17 Nov, 2025

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is S$155 per night from 20 Dec to 21 Dec
S$155
20 Dec - 21 Dec
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Wonderful Experience
Reviewed on 23 Nov, 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.
What to do in Old Bennington

Vermont RT 100: Self-Guided Driving Audio Tour
S$22
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.

