Angiomatosis is a diffuse vascular lesion which involves a large segment of the body in a contiguous fashion involving multiple tissues (e.g. subcutis, muscle, bone, adipose tissue etc.) in different planes. Such lesions usually present in the first two decades of life with female predilection and are commonly seen in lower extremities. It clinically mimics hemangioma or vascular malformation and its surgical removal is difficult because of its infiltrative nature and thus has high recurrence rate (90%). Therefore a precise histopathological diagnosis of angiomatosis is important to achieve a curative resection. Histopathologically it consists of proliferating blood vessels of varying caliber, infiltrating into the soft tissues. Proliferating capillaries are seen within or adjacent to major vessels. Few cases are reported in head and neck region. This article highlights three unusual cases of angiomatosis reported as benign lesions, in rare sites such as the malar region (predominantly infiltrating the adipose tissue), within the masseter (predominantly infiltrating the muscle) and in the mandible (infiltrating the bone). Histopathological differential diagnosis is also discussed.