In the 11th and 12th centuries the countship of Penthièvre (Breton: Penteur) in Brittany (now in the department of Côtes-d'Armor) belonged to a branch of the sovereign house of Brittany. Geoffrey I, Duke of Brittany, gave it to his brother Eudes in 1035, and the line formed a cadet branch of the ducal house of Brittany. Henry d'Avaugour, heir of this dynasty, was dispossessed of the countship in 1235 by the Duke of Brittany, Pierre Mauclerc, who gave it as dowry to his daughter, Yolande, on her marriage in 1238 to Hugh XI of Lusignan, Count of La Marche. John I, Duke of Brittany, Yolande's brother, seized the countship on her death in 1272.
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In 1337 Joan, Duchess of Brittany brought Penthièvre to her husband, Charles de Châtillon-Blois. They subsequently were proclaimed the duchess and duke of Brittany. War ensued. In the midst of the Breton War of Succession, in 1352, the États de Bretagne or Estates of Brittany were established. They would develop into the Duchy's parlement. In 1364, Joan and Charles lost decisively, and were left to keep Penthièvre.
When John V, Duke of Brittany in 1373 went in exile to England, the king of France Charles V named as lieutenant-general of Brittany his brother, the duke of Anjou, a son-in-law of Joanna de Penthièvre.
In 1420, duke John VI was kidnapped by the count of Penthièvre, son of Joanna of Penthièvre. John's wife, duchess Joanna de France besieged the rebels and set free her husband, who confiscated the Penthièvre's goods. In 1437 Nicole de Blois, a descendant of this family, married Jean II de Brosse, and was deprived of Penthièvre by Francis II, Duke of Brittany, in 1465 - thus undermining the Penthièvre family's position in the country. In 1488, at the death of the last male duke Francis II, the head of the Penthièvre family was Jean de Brosse (died 1502), grandson of Nicole de Blois the aforementioned, and he asserted their claim to the duchy, but Francis' daughter Anne succeeded.
The countship, which was restored to Sebastian of Luxemburg, heir of the Brosse family through his mother, was erected for him into a duchy in the peerage of France (duché-pairie) in 1569, and was afterwards held by the duchess of Mercœur, daughter of the first duke of Penthièvre, and then by her daughter, the duchess of Vendôme.
In 1582 Henry III of France, last living male-line grandson of Claude, Duchess of Brittany, made Philippe Emmanuel, Duke of Mercœur, his brother-in-law and a leader of Catholic League, governor of Brittany. Invoking the hereditary rights of his wife Marie de Luxembourg, he endeavoured to make himself independent in that province from 1589 onwards, and organized a government at Nantes, proclaiming their young son Philippe Louis de Lorraine-Mercœur "prince and duke of Brittany". He allied with Spain and defeated Henry IV of France's attempts to subjugate Brittany until March 20, 1598 when Mercœur was forced to surrender and subsequently went in exile to Hungary.
The duchess of Vendôme's grandson, Louis Joseph, duc de Vendôme, inherited Penthièvre in 1669, but it was taken from him by decree in 1687 and adjudged to Anne Marie de Bourbon, princess of Conti. In 1696, it was sold to the count of Toulouse, whose son, Louis Jean Marie de Bourbon, duc de Penthièvre, bore the title of duke of Penthièvre. This title passed by inheritance to the House of Orléans.