According to some legends, the monastery was established by Tsar Ivan Assen II. According to a notice, found on the monastery church’s apse, a church with a name “Holy Trinity” was built in this place in 1272. “St. Nikola” became an important religious centre during the period of the Second Bulgarian State. After the Ottoman domination was set over the Bulgarian lands the monastery was destroyed. In the late 17th century countrymen from the surrounding villages got an approval from the Turkish authorities to reconstruct the cloister.
In the early 19th century the last renewal of the monastery was done. The church was built in 1835 and in 1864 new residential buildings for the monastery’s monks were constructed. The monastery played an important role during the Bulgarian Renaissance period. In 1830 a literary school, which helped in the organization of the Hadzhi Stavri rebellion in 1860, was opened. The monastery took active part in the preparations for the April Uprising.
The church hosts a rich collection of icons. One of the most significant among them is the one of Our Lady, painted by Pope Vitan. The church itself is erected in the centre of the monastery yard which one can reach following the steep stone stairs.