4-star hotels in Brattleboro

Brattleboro is southern Vermont's counterculture holdout: bookstores, art co-ops and a farmers market that is a scene of its own, with the Connecticut River at the bottom of Main Street and Wantastiquet Mountain across the water. The Amtrak Vermonter stops downtown, and VT-9, the Molly Stark Trail, runs west over the mountains toward Bennington. It is a natural base for southeastern Vermont and for day trips into New Hampshire.

The 14 4-star properties on this shortlist are not downtown addresses. They sit out in the villages along the valleys: Putney Road in Brattleboro itself, Newfane, Putney, Dover, Marlboro and Jacksonville, with several a short drive from Mount Snow. That spread shapes who each one suits. Couples tend to take the inns, such as Four Columns Inn and Inn on Putney Road, while families and groups of friends are better served by the larger houses with kitchens, games rooms and pools, like the Newfane estate and the lake home in Jacksonville. Anyone wanting to walk to dinner should look at Putney Road, and anyone here to ski should look toward Dover and Marlboro.

Getting there and around

Brattleboro sits at the bottom of I-91 in Vermont's southeast corner, with VT-9, the Molly Stark Trail, running west over the mountains to Bennington. The Amtrak Vermonter stops downtown, 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. The nearest airports are Bradley near Hartford at about 90 minutes and Boston Logan at roughly two hours. Roughly two hours from Boston and around four from New York City, most of it on I-91. You can manage the town without a car, but anything up the valleys needs one.

When to go

Late September and early October for foliage, and summer for river swimming, paddling and the farmers market. Spring is wet but green and quiet, while winter is cold and inexpensive with the occasional snowstorm. Weekday stays are easier to book than fall weekends. The downtown scene runs year-round, and Harris Hill 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.