Yes. The Amtrak Vermonter stops downtown on its run between Washington, New York and St Albans, which makes Brattleboro one of the few Vermont towns you can reach car-free. The station is walking distance from Main Street lodging, restaurants and the museum.
Not for the town itself. Downtown, the river, the museum and the trailheads on the New Hampshire side are all walkable, and local buses cover nearby towns. You will want a car for the villages up the West River valley or the ski mountains at Mount Snow and Stratton.
Roughly two hours from Boston and around four from New York City, most of it on I-91. That proximity is why weekends and foliage season fill up faster here than in the northern half of the state.
The downtown scene runs year-round, and Harris Hill on the edge of town hosts one of the very few large ski jumps in the country, with a competition each winter. Mount Snow and Stratton are both under an hour away for downhill skiing.
Live prices for every hotel and inn in the area — free cancellation, updated daily.