Old Bennington Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Old Bennington
The Four Chimneys Inn
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 Williams Inn
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
Hotel Downstreet, an Ascend Collection Hotel
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
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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
