The monastery of St. Nicholas is located in the side of the road, between the river Trubezh and Yaroslavl highway. Near it stands the Smolensk-Kornilyevsky temple remaining from the monastery of STS.

The monastery of St. Nicholas as a men's monastery was founded around 1350 by St. Dimitry Prilutsky. In 1382, during the invasion of the Tatar hordes led by Khan Tokhtamysh the monastery was ruined and the entire city. Restored he was only in the XV century. Up to the time of Troubles, the monastery flourished, receiving considerable donations. The Polish-Lithuanian army was again ravaged her, and in 1613 came the elder Dionysius, rushing force for its revival.

At the end of the XVII century the monastery was delivered Korsunsky cross, which became its main Shrine (in our days is stored in the local Museum).

In 1704, in the monastery of St. Nicholas arrived future Archimandrite Pitirim, who with the support of the Peter the Great began to struggle with the dissenters (until 1738). When Pitirim was built the now demolished and recreated in a new form St. Nicholas collegiate Church, founded in 1680 under his predecessor Barlaam, who collected considerable funds for the construction of a new high hipped bell tower.

In the XVIII century the monastery completely re by stone buildings. Long home was built the Church of St. Nicholas (1680-1721 years) – high, five-domed Cathedral with three far delivered apses and wide Windows. In 1693 appeared the Cathedral belfry. Both these buildings have not survived: in 1923 the monastery was abolished and the main Cathedral and the bell tower was destroyed. For a long time there was livestock breeding.

After the monastery was returned to the believers, on the old Foundation was built a new St. Nicholas Cathedral, did not like the former and not seeking it, but became one of the main landmarks of the city. Replacing the bell tower came a massive three-span belfry. Church and bell tower were built in the new style by the architect Izhikov. not because old buildings are not preserved drawings, but for reasons of giving the cloister of the more classical forms", as the former Cathedral was built in Baroque style, not typical for Russia.

Very interesting one important event in the life of the monastery. It was founded as a men's monastery, but, in the opinion of the citizen of Pereslavl A. varentsova, in 1899 turned into a convent, for the reason that the number of brothers to the late nineteenth century had declined to a few people, and a nunnery was abandoned. Few women community headed by the abbess Antonia restored old buildings and built new ones. Now there is also a convent.

From old churches in the monastery survived two: Peter and Paul gate Church of the Annunciation Church and the refectory.

Peter and Paul Church was built with funds donated by the Moscow merchants brothers Kholshevnikov in 1750-ies in the Baroque style, with time, probably lost some of the details of its decor, but otherwise remained intact. The stateliness and aspiration up to the temple elongated dome, completed a narrow high drum with a small gilded cupola. In the dome on four sides there are some large Windows-lucarnes, similar in design and size to window of the quadrangle, on which rests the dome.

Annunciation Church with a low refectory was built to replace the burnt Kazan Church in 1748, also in Baroque style. It was built on donations of Moscow citizens Selagine. Its roof, like the dome of the Church of Peter and Paul, is extended upward and is decorated with tall, narrow drum, surmounted by a small cupola. At the corners of the square, set the drums are slightly smaller, with the exact same domes.

The monastery is surrounded by a low brick fence (1761 year) with ornamental turrets, some of which have been restored.

Restored not only the Church, but ancient stone and erected in 1902, cells and other outbuildings, and flows in which the monastic life.