Built in the 12th century by the monk Ugolino da Rocchione, Spedaletto Castle was born to host the pilgrims and wayfarers who travelled the old Via Francigena, one of the most important roads in Europe in the Middle Ages. Like many other fortified structures in the province of Siena, the complex fell under the influence of the Spedale di Santa Maria della Scala as of the 13th century. The original square-plan structure with corner towers and projecting stone corbels, was fortified between the late 15th century and the early 16th century, with the addition of a slight escarpment and embrasures for the use of fire arms.

The splendidly preserved castle today houses an agritourism facility.