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

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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 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

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 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

Hotel Downstreet, an Ascend Collection Hotel
See all 989 properties in Old Bennington
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

Vermont RT 100: Self-Guided Driving Audio Tour

S$22
per traveller
Vermont RT 100: Self-Guided Driving Audio Tour
See all activities in Old Bennington

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