Old Bennington Holidays
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Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is S$338 per night from 4 Jun to 5 Jun
S$338
4 Jun - 5 Jun
includes taxes & fees
9.4/10 Exceptional! (284 reviews)
"Had a great experience here. The staff was friendly and helpful. Chatting with the bartender and other guests at the bar over a nightcap made for an enjoyable evening. The room was clean and comfortable and the breakfast was fantastic."
Reviewed on 26 May, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is S$230 per night from 8 Jun to 9 Jun
S$230
8 Jun - 9 Jun
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Pool and hot tub"
Reviewed on 31 May, 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is S$427 per night from 15 Jun to 16 Jun
S$427
15 Jun - 16 Jun
includes taxes & fees
9.6/10 Exceptional! (631 reviews)
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."
Reviewed on 30 May, 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.
What to do in Old Bennington
Vermont RT 100: Self-Guided Driving Audio Tour
S$19
per traveller
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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
