Bennington is a working town with history, a college and lower prices; Manchester is polished, expensive and better for shopping, dining and the ski mountains. They are about 25 minutes apart on US-7, so you can stay in one and visit the other easily.
Most people drive: roughly four hours from New York City and around three from Boston. Albany International in New York is about an hour from Bennington and is by far the most convenient airport, and Amtrak's Ethan Allen Express reaches Rutland about an hour to the north.
It is VT-9, the roughly 40-mile route east from Bennington to Brattleboro over Woodford and the Hogback, named for the wife of the general who won the Battle of Bennington. It climbs to the highest sustained stretch of highway in Vermont and is a superb foliage drive.
The Battenkill through Arlington and Manchester is one of the most famous wild trout rivers in the East and also one of the hardest, with wary fish and heavy pressure. Orvis has been outfitting anglers in Manchester since 1856 if you want local guidance.
Live prices for every hotel and inn in the area — free cancellation, updated daily.