Old Bennington Holidays
Photo by Emily Whalen
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Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
9.4/10 Exceptional! (281 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 12 Jan, 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is S$265 per night from 2 Mar to 3 Mar
S$265
2 Mar - 3 Mar
includes taxes & fees
9.6/10 Exceptional! (582 reviews)
nice aesthetics
Reviewed on 24 Feb, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is S$156 per night from 26 Mar to 27 Mar
S$156
26 Mar - 27 Mar
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Room was clean and the bed comfortable. Staff is always friendly and helpful. Is convenient for our business there.
Reviewed on 28 Feb, 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.
What to do in Old Bennington
Vermont RT 100: Self-Guided Driving Audio Tour
S$22
per traveller
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