Old Bennington
Travel Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is CA $360 per night from Jul 26 to Jul 27
CA $360
CA $392 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (290 reviews)
"Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar"
Reviewed on Jul 24, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is CA $226 per night from Aug 24 to Aug 25
CA $226
CA $253 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,003 reviews)
"Loved this hotel. I can't rate it highly enough. Highly recommend."
Reviewed on Jul 25, 2026
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham VT
The price is CA $701 per night from Jul 26 to Jul 27
CA $701
CA $1,203 total
Jul 26 - Jul 27
includes taxes & fees
Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna, and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ...
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."
Reviewed on May 25, 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.
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls NY
Stay at this vacation home in Hoosick Falls. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Bennington Center for the Arts and Unihog ...
9.8/10 Exceptional! (107 reviews)
"Very secluded and nice!"
Reviewed on Jul 4, 2026
24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views
Stamford VT
Stay at this vacation home in Stamford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Massachusetts Museum of Contemporary Art and Clarksburg ...
10/10 Exceptional! (1 review)
"Great house, great location, and communication was excellent"
Reviewed on Jun 29, 2026
Cozy 2-bedroom cabin near Mount Snow 3 min drive
Dover VT
Stay at this cabin in West Dover. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Mount Snow and Nitro Express ...
9.8/10 Exceptional! (16 reviews)
"nice- thanks"
Reviewed on Jul 2, 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.
Stay near popular Old Bennington attractions
Things to do
Vermont RT 100 App-Guided Driving Audio Tour
CA $24
per traveller
