A weekend away at one of the best Berkshires hotels or rental homes is the perfect year-round escape for scenic mountain views and historic charm, whether you choose to bunk at a bucolic inn or an Airbnb from the 1800s that comes blessed with a moody, Wes Anderson-esque design scheme. Concentrated in western Massachusetts and parts of Connecticut, plus less than a three-hour drive from New York City, the region boasts hiking trails just as incredible as its antiquing scene, making it the ideal weekend departure for any kind of traveler in the tri-state area and even further afield. Fans of the History Channel will love a stay in Stockbridge, where a picturesque small town highlights the history of the mountainous region.