The surname Winterle has its origins in Germany, likely arising during the Middle Ages. The name is thought to be locative, indicating that it originated from a place, possibly a small settlement or a geographical feature. Given the German linguistic roots, the name is derived from the Old High German word "wintar" meaning "winter" and the diminutive suffix "le". This suggests that the name could either refer to a person who lived in a particularly cold area or had some association with the winter season.

The earliest references to names similar to Winterle can be found in records from the late 12th or early 13th century, particularly in the Swabian region, an area in southwest Germany known for its distinct dialect and medieval townships. One of the earliest appearances in written form is in a document from 1276, listing a Heinrich Winterlin as a landholder in the village of Donaueschingen. The suffix "lin" is a common diminutive in Alemannic German, closely related to "le".

Historical accounts and parish records between the 13th and 15th centuries feature various spellings of the surname, such as Winterli, Winterlein, and Wintarl. These variations generally represent the same familial lineages and regional prose peculiarities. In 1437, a Hans Winterle is recorded in Augsburg as a master craftsman, indicating the family's involvement in trade and skilled labor.

Noteworthy individuals include Johann Winterle, a noted merchant who lived from 1510 to 1564. He played a significant role in the commercial trade routes between Germany and Italy. Another eminent figure was Maria Winterle (1625-1689), whose charitable works during the Thirty Years' War were well-documented in ecclesiastical annals.

In the Enlightenment period, a Wilhelm Winterle (1732-1798) emerged as a scholar and writer, contributing to early German literature and philosophy. His works included a notable essay on the socio-cultural impact of seasonal weather patterns on rural communities.

The 19th century saw the name Winterle in various European records as families migrated to new regions due to economic opportunities or political pressures. One such individual, Karl Winterle, born in 1812, became a prominent figure in the industrialization of Bavaria before his death in 1878.

Despite its variations and adaptations, the name Winterle encapsulates a legacy of historical relevance tied to Germany's medieval landscapes, societal roles, and its people’s resilience and contributions through centuries of European history.