The monastery in the village of Kovylay was established thanks to the charity of Princess Nadezhda Danilovna Bibarsova, a representative of an ancient Tatar family that converted to Orthodoxy in the late 17th century. The village of Kovylay, located in the Krasnoslobodsky district of the Penza province, emerged in the late 16th and early 17th centuries as part of the first defensive line. Until the Time of Troubles, the village was free, but later, as a result of grants, it ended up in the possession of Tatar landowners who guarded the Temnikov and Saransk defenses. The owners who converted to Christianity became Russian princes, while those who did not migrate. The godmother of Nadezhda Danilovna, Princess Evdokia Borisovna Kugusheva, lived in the village and was acquainted with the founder of the Diveevo community, Agafya Semyonovna Melgunova, whom she often visited. Evdokia helped the sick and the poor, and Nadezhda followed her example, distributing relics and assisting those in need.

Before 1614, a wooden Nikolskaya church was built in Kovylay, and in 1699, a new Church of the Nativity of Christ was constructed. At the initiative of Princess Nadezhda and her relatives, a stone Church of the Nativity of the Most Holy Theotokos was erected in 1826. This church became the foundation for the monastery, around which the first group of lay sisters gathered.

The architecture of the church is an example of late classicism with simple geometric forms. The official organizer of the almshouse was Prince Y. D. Bibarsov, but in fact, it was managed by N. D. Bibarsova. She received the blessing of three elders to establish the monastery and worked on its arrangement from 1826 to 1833. In 1833, after the death of her brother, she became the full owner of Kovylay and directed her inheritance towards the development of the monastery.

In 1834, the first 12 sisters settled in the monastery. Between 1842 and 1847, Princess Bibarsova strengthened the material base of the monastery by transferring land and a house to it. In 1847, the donations and the charter of the monastery were approved. Under the guidance of the abbess Tatyana Martynovna Meshcherina, the monastery endured difficult years but became a full-fledged monastery.

In the 1860s, the monastery was recognized as a sisterhood, and in 1862, the construction of new buildings and churches began. Princess Bibarsova died in 1862, but her work continued. In 1875, the monastery was granted the status of Trinity, and by 1884, it was headed by Abbess Feofania. Under her leadership, the monastery flourished, workshops were established, an icon-painting school was created, and social programs were initiated.

By the 1910s, the monastery had become one of the largest in the region, with numerous buildings and an estate. However, in 1918, it began to be destroyed, and in 1926, the monastery was closed. In 1927, Abbess Viktorina was arrested and executed.

Today, a women's monastery has been revived in Old Kovylay, and the Church of the Nativity of the Theotokos has been transferred to the monastery. Restoration work is being carried out with donations from parishioners, and since 2002, the monastery has been headed by nun Magdalina. In 2004, a house church in honor of the icon of the Mother of God "Joy of All Who Sorrow" was consecrated.