The 125-room, three-pearl Red Lion Inn is a charming, historic property on Main Street in Stockbridge, one of New England’s most iconic small towns. The individually decorated rooms and public spaces feature an impressive collection of antiques and period decor. Amenities such as room service, year-round heated outdoor pool, authentic taverns, and in-house masseuse enhances its appeal, though breakfast costs extra. The inn offers a wide variety of accommodations, ranging from cottages to rooms with shared bathrooms, but some rooms look a bit tired, even for a historic property. For an elegant boutique experience at comparable rates, consider the Gateway Inn in nearby Lenox.