“When Machiavelli came to the end of his life, he had a vision shortly before giving up the ghost. He saw a small company of poor scoundrels, all in rags, ill-favoured, famished, and, in short, in as bad plight as possible. He was told that these were the inhabitants of paradise, of whom it is written, Beati pauperes, quoniam ipsorum est regnum caelorum.”

After they withdrew, innumerable serious and majestic personages appeared, who seemed to be sitting in a senate-house and dealing with the most important affairs of state. Among them he saw Plato, Aristotle, Seneca, Plutarch, Tacitus, and others of similar character; but he was told at the same time that those venerable personages, notwithstanding their appearance, were the damned, and the souls rejected by heaven, for Sapientia huius saeculi, inimica est Dei.. After this, he was asked to which of the groups he would choose to belong; he answered that he would much rather be in Hell with those great geniuses, to converse with them about affairs of state, than be condemned to the company of the verminous scoundrels that he had first been shown.
This account of Machiavelli's "Dream" was not published until a century after his death, in Etienne Binet's Du salut d'Origene (1629).
There is an earlier but more oblique reference in a letter written by Giovambattista Busini in 1549: "Upon falling ill, [Machiavelli] took his usual pills and, becoming weaker as the illness grew worse, told his famous dream to Filippo [Strozzi], Francesco del Nero, Iacopo Nardi and others, and then reluctantly died, telling jokes to the last.".
The "Dream" is commonly condensed into a more pithy form, such as "I desire to go to hell, and not to heaven. In the former place I shall enjoy the company of popes, kings, and princes, while in the latter are only beggars, monks, hermits, and apostles".
Disputed
Source: Blessed are the poor, for theirs is the kingdom of heaven
Source: The wisdom of this world is the enemy of God
Source: [Estienne, Binet, Du Salut D'Origene, 1629, Paris, Sebastien Cramoisy, 359-361, French, https://books.google.com/books?id=1yjDNfQatgQC&q=Plutarque&f=false]. Original French: On arrive à ce detestable poinct d'honneur, où arriva Machiauel sur la fin de sa vie: car il eut cette illusion peu deuant que rendre son esprit. II vit un tas de pauures gens, comme coquins, deschirez, affamez, contrefaits, fort mal en ordre, & en assez petit nombre, on luy dit que c'estoit ceux de Paradis, desquels il estoit ecrit: "Beati pauperes, quoniam ipsorum est regnum cælorum". Ceux-cy estans retirez, on fit paroistre vn nombre innombrable de personnages pleins de grauité & de majesté, on les voyoit comme un Senat, où on traitoit d'affaires d'estat, & fort serieuses, il entrevid Platon, Aristote, Seneque, Plutarque, Tacite, & d'autres de cette qualité. II demanda qui estoient ces Messieurs-là si venerables, on luy dit que c'estoient les damnez, & que c'estoient des ames reprouuées du Ciel, "Sapientia huius sæculi, inimica est Dei". Cela estant passé, on luy demanda desquels il vouloit estre. II respondit, qu'il aymoit beaucoup mieux estre en enfer auec ces grands esprits, pour deuiser auec eux des affaires d'Estat, que d'estre auec cette vermine de ces belistres qu'on luy auoit fait voir.
Source: [Lettere di Giovambattista Busini a Benedetto Varchi, Italian, Giovanni Battista, Busini, Gaetano Milanese (ed.), Florence, Felice le Monnier, 1860, 84-85, https://books.google.com/books?id=d5EKAAAAIAAJ&q=%22queste+pillole%22#v=snippet&q=%22queste%20pillole%22&f=false]. Original Italian: Ammalato cominciò a pigliar di queste pillole, ed a indebolire ed aggravar nel male; onde raccontò quel tanto celebrato sogno a Filippo, a Francesco del Nero ed a Iacopo Nardi, e ad altri, e cosi si morì malissimo contento, burlando.
Source: [The Last Words (real and Traditional) of Distinguished Men and Women, Frederic Rowland, Marvin, 178, Revell, 1902, https://books.google.com/books?id=SrEVAAAAYAAJ&pg=PA178&dq=Hell+Heaven+%22enjoy+the+company+of+popes%22&hl=en&sa=X&ved=0ahUKEwj7x9SZzdDJAhUE-2MKHaO_CBkQ6AEIHDAA#v=onepage&q&f=false]