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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 11 Nov to 12 Nov
S$188
11 Nov - 12 Nov
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Good facility in a not great neighborhood. Very helpful and friendly staff."
Reviewed on 12 Oct, 2025
The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is S$307 per night from 2 Nov to 3 Nov
S$307
2 Nov - 3 Nov
includes taxes & fees
9.6/10 Exceptional! (520 reviews)
"Lovely clean room with a fabulous shower. Tea/coffee available 24 hours with a choice of milks which is great. Refillable glass bottle in the room to collect fresh water which meant no plastic bottles. Plenty of parking, cosy lobby and restaurant food excellent."
Reviewed on 10 Oct, 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.
