It is believed that the first monastery in this place was founded some 2km to the north of the present-day buildings, in an area called The Little St Archangel. The Assen and Petar brothers from Turnovo were its founders. In the 14th century, the holy place was one of the main centers of Hesychasm and sheltered many monks. At the beginning of the 15th century, the monastery was destroyed by the invading Ottoman troops. Later on, it was reconstructed on a neighboring site, known as the Big St Archangel, but the fate of this monastery was the same. The Dryanovo monastery was restored anew at the end of the 17th century, this time in its present-day place. The main church of that time had a single nave and was half-hidden in the ground. It was standing very near to the present-day church; besides it, there was also a secondary shrine.
The renovation of the monastery was started at the time of father Rafael, during the 40es of the 19th century. The current residential buildings rising from the side of the river were built at that time, while the new church was finished in 1845. Gradually, the renovated Dryanovo monastery became a religious and cultural centre and one of the largest and well-kept cloisters in the region of Turnovo.
Like many other monasteries in Bulgaria, the Dryanovo monastery took active part in the Bulgarian revolutionary activity against the Ottoman rule. Famous rebel leaders such as Vassil Levski and Georgi Izmirliev often visited the cloister. There was a secret storeroom for food and arms, used later at the time of April uprising. After the battle with the Turkish troops the monastery was again set on fire. The most recent reconstruction of the complex was carried out shortly after the Liberation. A new residential part and a museum were added. The bell-tower was erected in 1925.