Cloister's flag Cloister Inn, Princeton's 16th eating club, was founded in 1912. It initially occupied Cottage Club's second building, which had been recently vacated by Tower Club. Cloister remained in this structure through the first World War, selling it to the now-defunct Court Club in 1920. The funds from this sale were used to purchase the current Cloister lot, between Cap and Gown and Charter.

Cloister had begun contemplating a new home as early as 1920 and rejected two designs. The first, by Robert Henry Scannell '15, suggested a "cloister" in its plan for the entrance, a triple arch, but was otherwise undistinguished. The second was far more ambitious. Designed by Albert Relsen of Philadelphia, it featured a medieval cloister to the rear of the building. In this regard, it resembled a smaller scale version of Holder Hall on the campus (see image at right). But for financial reasons, it was not built. Scannell submitted a second design in 1923 that was adopted and the building was completed by the spring of 1924. Executed in the local stone (Lockatong argillite, or "Princeton stone") used in many of the University's dormitories, Scannell's design reflected the University's preference for a generic "Collegiate Gothic" style that incorporated and amalgamated medieval English precedents. The dominant element in Scannell's design for Cloister is the row of pointed arches that face Prospect Avenue. (These arches are continued past the enclosed portion of the building to frame a covered patio.) The carved, arched doorway also contributes to the medieval flavor of the facade. Enormous stone chimneys complete the effect.

Dining room at Cloister Cloister's public elevation squarely places it in the tradition of the later clubs, which took their inspiration from the University itself rather than the earlier clubs. In this, Cloister is most closely related to Dial Lodge (1917) and Key & Seal (1925), both of which are now out of operation. In 1972, Cloister closed temporarily and became an alternate dining facility for underclass students as well as an alumni center. This was short-lived, however, because in 1977 a student initiative reopened the building as an eating club, and it has been in operation ever since.

Cloister's backyard Cloister experienced major changes in the 1980s with the addition of a game room and outdoor deck on the main floor, and expanded space in the lower-level dining room. In the early 1990s, an outdoor hot tub was incorporated into a deck on the side of the building. More recently, Cloister received mentioning in Ian Caldwell and Dustin Thomason's 2004 bestselling novel The Rule of Four. Caldwell, a 1998 graduate of Princeton, was a member of Cloister.