Old Bennington Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Emily Whalen
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 5.136.032 ₫ per night from 3 Mar to 4 Mar
5.136.032 ₫
5.736.948 ₫ total
3 Mar - 4 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 2.883.839 ₫ per night from 30 Mar to 31 Mar
2.883.839 ₫
3.221.248 ₫ total
30 Mar - 31 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.
Popular places to visit
Bennington Battle Monument
Learn about the local history of Old Bennington with a stop at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Old First Congregational Church
Find out about the history of Old Bennington when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
You can spend an afternoon exploring the galleries in Hemmings Motor News Car Lover's Convenience Store & Vehicle Display during your travels in Bennington. While you're here, you can savour the cosy cafes.
