9. Ayllón:
Yet another historical gem in Spain’s treasure trove, Ayllon is best known for the 1411 treaty signed between Portugal and Castile concluding the wars of the Interregnum. Ayllon is also a declared Property of Cultural Interest. Cobblestone streets lined by majestic edifices and traditional homes will transport you back to the medieval times. Relics of the past include an arch with 17th-century shields, the Palace of the Contreras with a gorgeous Isabellian facade, 16th century City Hall and the Romanesque church of Saint Michael.
If you visit Ayllon towards the end of July, you can be a part of the Ayllón Medieval Festival in which locals dress up in period costume and an interesting medieval market is organized.
A great list but I would also include some places in Extremadura!