Old Bennington Trip
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Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
9.6/10 Exceptional! (223 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 ₹17,124 per night from 1 Mar to 2 Mar
₹17,124
₹19,127 total
1 Mar - 2 Mar
includes taxes & fees
9.6/10 Exceptional! (572 reviews)
Clean
Reviewed on 31 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is ₹11,581 per night from 24 Feb to 25 Feb
₹11,581
₹12,936 total
24 Feb - 25 Feb
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Nice location and beautiful lobby.
Reviewed on 27 Jan 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.
Prospect Mountain Nordic Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and cafes.
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