Windsor County’s town of Chester is best known for its Stone Village and Chester Village Historic Districts, both of which are listed in the National Register of Historic Places. Stone Village got its name for the predominance of granite houses, and Chester Village features a typically New England federal and colonial aesthetic. A popular tourist destination for its character, Chester is home to the Chester Fall Festival in September, charming inns, antique shops, galleries and great restaurants. Additionally, Chester caters for cyclists, boaters and skiers, lying with driving distance of Okemo, Mount Snow and Killington.
Where to stay: Breathe in the fresh air at this idyllic cabin house retreat just outside Chester. Housing up to eight guests, it’s comfortable, private and provides easy access to the New England countryside.