Name: Hotel Downstreet, an Ascend Collection Hotel
Price range: CA $155
Rating: 8.8

Photo by Emily Whalen

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Your Old Bennington Vacation

The rich history and spectacular views are just the start of the things Old Bennington has on offer. Experience the very best of this interesting city the way you want with a personalized Old Bennington vacation package. If your trip to Old Bennington includes a little sightseeing, check out famous attractions like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Expedia will help you escape the everyday. Tailor your vacation to Old Bennington to suit your travel style, whatever that may look like.

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Old Bennington Hotel Deals

The Four Chimneys Inn

21 West Road Bennington VT

9.6/10 Exceptional! (223 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 Williams Inn

101 Spring Street Williamstown MA

Fully refundableReserve now, pay when you stay

CA $267

CA $299 total

Feb 19 - Feb 20

includes taxes & fees

9.6/10 Exceptional! (573 reviews)

A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff.

Reviewed on Feb 7, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

CA $155

CA $173 total

Mar 17 - Mar 18

includes taxes & fees

8.8/10 Excellent! (1,001 reviews)

Spotless and front desk staff...friendly and accommodating

Reviewed on Feb 11, 2026

See all 1,010 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.