In 1411, the building began life as a convent: St. Catherine's Convent occupied the southern part of the property, while St. Cecilia's Convent occupied the northern part. At that time, Amsterdam had many convents and monasteries, whose designs featured courtyards and enclosed gardens. Relics of the plan are still in evidence at the Grand.

In 1578, after the Reformation, Protestantism was adopted as the official religion of Holland; the convents were confiscated as property of the city. The convent of St. Cecilia was converted into a guest house called "Princen en Groote Heeren" (Princes and Gentlemen Standing) and was later renamed "Princenhof" (Princes' Court). It was used as lodging for the esteemed guests of city officials, such as members of the European royal family.

During the 17th century, part of St. Catherine's Convent was bequeathed to the Admiralty of Amsterdam, a local administrative council. In 1647, the city of Amsterdam built a new accommodation called "Oudezijds Herenlogement" (Old Side Hostel for Gentlemen). Since Princenhof was no longer needed as a hotel, it was converted into a town hall, and served as the seat of Amsterdam's government for several years.

In 1655, when a new structure was built to house the City Hall, the Admiralty took ownership of the entire property. The council built a structure between St. Cecilia's and St. Catherine's convents and named it as the main building. The imposing facade of this main building is now the entrance to the Grand.

When the French occupied Holland in 1806, Emperor Napoleon chose his brother Louis as King of Holland. Two years later, in 1808, Louis made the new town hall on Dam Square his royal palace and forced Amsterdam city officials to move the town hall to the Princenhof. After Holland regained its independence from France, the Royal Palace became the residence of the country's ruler and the Princenhof remained Amsterdam's city hall for the next 180 years.

Holland was occupied by Germany during World War II. The Nazis abolished the Amsterdam city council and replaced it with officials appointed by the Germans. Upon Amsterdam's liberation in 1945, the city hall was once again the seat of government for the city.

In addition to its various roles over the centuries, the Princenhof has also participated in the evolution of art in Amsterdam. In 1949, a renowned artist, Karel Appel, was commissioned to paint a mural in the town hall. While the new artwork was not well received at the time, both murals are considered priceless art treasures of the city today.

After World War II, the Princenhof was considered ill-equipped to serve as the seat of government for a large mercantile city. Construction of a new city hall began several decades later and was opened in 1987. When the Princenhof no longer served as Amsterdam's seat of government, its fate was uncertain. Citizens were concerned that the art housed there would be lost or sold, so the City Council passed a resolution that the priceless cultural objects would be inviolable.

In 1992, the building was transformed into the Sofitel Legend The Grand Amsterdam hotel. No expense was spared to renovate and preserve the historic features of the structure. The restoration has maintained the flavor of the Princenhof, whose walls are adorned with reproductions of French and Dutch coats of arms and portraits of Dutch nobility.

The Grand features 179 contemporary accommodations, including 52 luxury suites with exclusive butler service. A harmonious blend of traditional and contemporary French design, including typical Dutch style elements. The site's rich heritage has been carefully preserved, while ensuring that accommodations are equipped with the modern conveniences that today's traveler expects.