Old Bennington Holidays

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Top hotels in Old Bennington

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
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 Four Chimneys Inn
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is €190 per night from 1 Dec to 2 Dec
€190
1 Dec - 2 Dec
includes taxes & fees
9.6/10 Exceptional! (544 reviews)
Bb

Reviewed on 17 Nov 2025

The Williams Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is €103 per night from 20 Dec to 21 Dec
€103
20 Dec - 21 Dec
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Wonderful Experience

Reviewed on 23 Nov 2025

Hotel Downstreet, an Ascend Collection Hotel
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.

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