Clan Chisholm had its origin outside Scotland. The first Chisholm to appear in the records of Scotland was Alexander de Chesholme, who witnessed a charter in 1248/49.
The early Scottish Chisholms were not to be found in the Highlands, but owned land near the English border. In 1296 Richard de Chesholme was described as "of the county of Berwick", while in 1335 Alexander de Chesholme was called "Lord of Chesholme in Roxburgh and Paxtoun in Berwickshire."
Apart from the property they owned, nothing is known of these men, but with Alexander's son Robert the first connection is made with the Highlands. Robert married the daughtr of another Border laird, Sir Robert Lauder of the Bass. In 1329, Sir Robert Lauder wes sent as Justicar of the North and Constable of Castle Urquhart. In return for his good service, especially against the King's enemies in 1333, Lauder was given the lands of Quarrelwood, near Elgin, and others at Cantray, near Nairn.
These lands of Quarrelwood and Cantray were to pass through Robert Chisholm and his wife to their own son Robert. This Robert fought against the English at the battle of Nevilles Cross in 1346, was taken prisoner with King David II and probably not released until eleven years later whrn his royal master returned to Scotland. In 1359 Robert Chisholm succeeded his Grandfather as Constable of Castle Urquhart, and later became Sheriff of Inverness and Justicar of the North. This Robert was the last Chisholm to hold lands in both the North and South of Scotland. He divided his estates among his younger children.
In 1368 Robert's eldest son, Alexander, married an heiress, Margaret del Ard, the Lady of Erchless. Margaret's dowry included land in Forfar, Perth, Lanark, Aberdeen and Invernessshire. Their son, Thomas married the daughter of Lachlan Mackintosh of Mackintosh in about 1400. It is possible that Comar and Strathglass were part of her dowry, although there is no evidence that the Mackintoshes ever owned land so far north-west of Loch Ness.