Bennington is a working town rather than a resort village, with a decent supply of roadside and chain lodging along US-7 and VT-9. You give up the picture-postcard main street of a Woodstock or Manchester, but you get a real town with lower rates and the same mountains next door.
Albany International in New York is the practical choice at roughly an hour by road, and it usually beats Burlington on both price and drive time. Hartford's Bradley and Boston Logan are both around two and a half to three hours.
It works for the southern mountains: Mount Snow is around 45 minutes east on VT-9, and Stratton and Bromley are within an hour north. Room rates here are typically well below on-mountain lodging, at the cost of a daily drive over the pass, which can be slow after snow.
A full day covers the monument, Old First Church, the museum and the North Bennington bridges without rushing. Half a day is enough if you skip the museum.
Live prices for every hotel and inn in the area — free cancellation, updated daily.