Old Bennington Vacations

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Find the Best Old Bennington Vacation Packages

Old Bennington Hotel Deals

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
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 Jan 12, 2026

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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 ₩283,818 per night from Mar 2 to Mar 3
₩283,818
₩317,025 total
Mar 2 - Mar 3
includes taxes & fees
9.6/10 Exceptional! (582 reviews)
nice aesthetics

Reviewed on Feb 24, 2026

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 ₩159,361 per night from Mar 26 to Mar 27
₩159,361
₩178,006 total
Mar 26 - Mar 27
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 Feb 28, 2026

Hotel Downstreet, an Ascend Collection Hotel
See all 1,005 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.

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