The Red Lion Inn

A Stockbridge landmark since 1773, The Red Lion Inn is classic New England — rocking chairs on a wide front porch, antique teapot collections, and 250 years of guests ranging from five U.S. presidents to Nathaniel Hawthorne. The main inn has 108 individually decorated rooms, with additional accommodations spread across a handful of historic village houses, including a converted firehouse that appeared in a Norman Rockwell painting. Dining covers a lot of ground: the candlelit Main Dining Room for New England fare, Widow Bingham’s Tavern for something more casual, the Lion’s Den for live music and local spirits, and a flower-filled Courtyard in warmer months. The wine list has held a Wine Spectator Award of Excellence for over 20 consecutive years. A year-round heated outdoor pool, fitness center, and proximity to the Berkshires’ arts scene, hiking, and ski slopes round it out.