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Local tradition holds that Saydnaya means ‘Halting place of the gazelle’. The place name has also been thought to mean Our Lady the New, from the Greek nea, ‘new’, and the Arabic sayyida, ‘lady’. However, the word sayd is generally related to hunting, and naya is a typical place suffix in Syriac; therefore, Saydnaya probably means simply a hunting place. Indeed, in ancient times, a temple of Saydoun, the Phoenician god of the hunt, stood in this once densely forested region. Under later Christian and Arabic influence, perhaps the name may have been thought to mean the ‘place of the Lady’. The Hellenistic era name for the region centered in the Barada Valley was Abilene: the local tradition has thus long held it as the site where the grave of Abel, slain brother of Cain, lies. Scholars consider it likely that the capital of Abilene was the city of Saidnaya.

Long a center of Christian pilgrimage, pilgrims from all over the world seek Saidnaya for renewal of faith and for healing. Also located in the convent of Saidnaya is an icon of the Holy Mother and Child known as the Shaghurah and reputed to have been painted by Luke the Evangelist which is believed to protect its owners from harm in times of danger. Numerous accounts of miraculous healings have been reported, some which are documented in writing by those who experienced them throughout history. Saidnaya has about more than 40 chapels and monasteries and the most famous one is the convent of the Virgin Mary. The weather is cold and snowy in winter, while it is warm and has fresh air in summer. Surviving vestiges of caves, grottos and ancient places in and around Saydnaya indicate that it was inhabited by different civilizations from the early Stone Age, with artifacts from Aramaic, Greek, Syriac, Roman, and Arab times.

Saidnaya's origins are in ancient times, and the town has been inhabited since at least the sixth century BC when it was known by its Aramaic name, Danaba.

In the late 8th century, a certain venerable Marina was abbess of the convent, and she was widely revered for her piety and sanctity of life. It happened that a hermit monk, a Greek pilgrim from Egypt named Theodore, stopped at the convent on his way to the Holy Land. When he was leaving, Abbess Marina asked him to buy in Jerusalem a precious and fine icon of the Holy Virgin. While at Jerusalem, he utterly forgot the task entrusted to him and started on his return journey. However, when he had not gone far from the city, he was stopped short by an unfamiliar voice: "Have you not forgotten something in Jerusalem? What have you done in regard to the commission from Abbess Marina?" Monk Theodore returned at once to Jerusalem and found an icon of the Theotokos. During the journey back to the convent, he was astounded by the miracles accomplished through the icon. He and his whole caravan were ambushed by bandits, and then attacked by wild beasts. Amidst these dangers, the hermit always invoked the aid of the Holy Virgin while holding her icon, and he and all the caravan were saved from every peril. These events tempted him to keep the valuable icon for himself, and he decided to bypass Saidnaya and sail back to Egypt. However, he was unable to set sail, for such a fierce storm arose, it seemed the ship would inevitably sink. His conscience was pricked, and he quickly left the ship and returned by way of Saidnaya. After spending four days in the convent, he was again possessed by an irresistible desire to make the icon of the Mother of God his own. He apologized to the abbess, pretending that he had been unable to buy the required icon, and then he decided to leave the convent secretly. The next morning, as he was about to set out on the journey back to his own country and approached the convent gate, he was amazed to find that an invisible power barred his way, and it was as though a stone wall stood where the gate should have been. After many futile attempts, he was forced to hand the icon over to the abbess, confessing his intention. With tears of gratitude she glorified the Lord and His All pure Mother. Today the holy Icon is visited by pilgrims seeking the Virgin Mary's blessings as it is believed to grant (or at least intercede for) healing and fertility miracles. It is notable that Syrian Muslims often visit and pray before the Icon as well.

According to the tradition, emperor Justinian I, while crossing Syria with his troops either on his way to the Holy Land or on a campaign against the Persians, came to this desert, where his army encamped and soon suffered thirst for lack of water. When they despaired, the emperor saw a beautiful gazelle off in the distance. He vigorously gave chase, hunting the animal until it tired and stopped on a rocky knoll and approached a spring of fresh water, but without giving the emperor the opportunity to shoot it. Suddenly, it transformed into an icon of the Theotokos, which shone with a brilliant light. A white hand stretched forth from it and a voice said, "No, thou shalt not kill me, Justinian, but thou shalt build a church for me here on this hill." Then the strange heavenly light and majestic figure disappeared. Upon his return, Justinian related what he had seen to his subordinates and ordered them immediately to draw up a plan for the contemplated church. After some time had passed and the architects were unable to resolve the problems of the plan, the Holy Virgin — the gazelle — reappeared to Justinian in a dream and confided a magnificent plan to him for a convent, of which she would be the protectress. It is said that the basic structure of the convent follows this plan to this day. The convent soon gained such renown that it came to be ranked second only to Jerusalem as a place of pilgrimage, and nuns from every corner of Syria, Egypt, and other lands flocked to it. The holy icon El Chagoura appeared many years after the convent was constructed. In From the Holy Mountain, William Dalrymple notes that in Arabic, Saidnaya means both "our lady" and "hunting place", and the legend is likely related to this.

Magister Thietmar, a German pilgrim, wrote of his pilgrimage to Saidnaya, devoting four pages to a description of the icon of Holy Mother and Child found at the convent. He describes the origin story behind the icon and its special properties, and how a holy oil emitted from the breasts of the Virgin Mary is believed to be a miraculous oil that can heal the sick. In September 1240, after Thibaut de Champagne concluded a treaty with the sultan of Egypt, the Benedict of Alignan made a pilgrimage to St. Mary's of Saidnaya with the sultan's permission. The trip is seen as evidence of both Saidnaya's importance to Christian pilgrims in the thirteenth century and the relative safety of travel for Christians in Muslim areas during this time. Chronicles from the thirteenth century also report that Templar Knights would go to the mountain monastery in Saidnaya to collect holy oil for Templar churches in Europe.

To the west of Saidnaya, the government has a military prison with estimated of 14,000 prisoners. The prison lies 30 km on the outskirts of Northern Damascus. In February 2017 Amnesty International released a report saying: "that between 5,000 and 13,000 people were extra judicially executed at Saydnaya between September 2011 and December 2015." On May 15, 2017, the US State Department reiterated the charge of 50 secret executions a day, concealed by subsequent cremation on site.