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The Fortress overhangs the medieval hamlet of Castiglione d'Orcia.
Castiglione D'Orcia seems to be the most ancient settlement of the area, although notices of the presence on site of a Parish Church and then of a castle dates back only from the Middle Age. The history of this castle is closely connected to the controversies over its control which existed between the monks of the Abbey of San Salvatore and the Aldobrandeschi family. The small fortress controlled the ancient road that, from the Mount Amiata, leads to the Val d'Orcia, the most important medieval road for the communications from and toward the Maremma. The nearby, only at a few hundred meters, of the mighty Rocca of Tentennano limited the control that the Rocca Aldobrandesca could practice on the Val d'Orcia and on the Francigena Road that crossed it, due to the fact that its 'twin' rose in a better strategical position for this purpose.
In the 13th century the area began to interest the big cities of Siena and Grosseto. After years of hard struggles, was the city-state of Siena to take control on Castiglione, subdued in 1251, and the other fortresses of Val D'Orcia, acquired between 1254 and 1258. The Sienesi reinforced all the structures of the fortification. The feudal family of Salimbeni had in fief from Siena this part of the Val d'Orcia, thanks to the services given to the Republic in the Monteaperti battle fought against the Florentine army. Only in 1419 Siena, after many failed attempts, subtracted these castles at the dominion of the Salimbeni that were becoming, with their expansionist aims, a menace for the chief town.
The fortification lies today in ruins for the state of abandonment in which has been left from the end of the 'War of Siena' of the 16th century, but also for the serious damages suffered during the bombardments of the second world war. We can still admire the neatly squared stones used in the construction of the octagonal shaped keep and we can easily imagine its original aspect: it had to seem a classical-build medieval fortresses divided in two courtyards, with the great external enclosure able to contain the population in case of yielding of the city walls. Fortunately the underlying village has been recently object of a main restoration.
In the last years the whole complex of the rocca has been object of massive works of restoration. The area has been cleaned from the vegetation, the outer and the keep walls consolidated.