Old Bennington Holidays
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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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is Rp2.074.157 per night from 27 Jan to 28 Jan
Rp2.074.157
Rp2.316.834 total
27 Jan - 28 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Courteous staff
Reviewed on 19 Dec 2025
The Williams Inn
101 Spring Street Williamstown MA
The price is Rp3.308.915 per night from 13 Jan to 14 Jan
Rp3.308.915
Rp3.696.046 total
13 Jan - 14 Jan 2026
includes taxes & fees
9.6/10 Exceptional! (554 reviews)
Staff was courteous. Room was clean and felt...warm and inviting. Decor is classy cozy and clean. Every floor has coffee station with tea and coffee instead of in the room making it convenient before venturing out. The Barn is nice. I visited in winter so the ground, firepit and pool, were closed ...
Reviewed on 22 Dec 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
Harmon Hill
You can take time to visit Harmon Hill during your travels to Bennington. While you're here, you can savour the cosy cafes.
What to do in Old Bennington
Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway
Rp284.583
per traveller
94% of travellers recommend
Vermont RT 100 Self Guided Driving Audio Tour
Rp284.583
per traveller
Green Mountain Adventure Challenge Passes
Rp1.256.250
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
