Boleskine House has been an eerie spot basically from its inception.

It is allegedly built atop the ruins of an old church manse that became ruined during the eighteenth–century. The house looks over Boleskine Cemetery at the foot of the hill, which hosts old war graves from the Jacobite rebellion. The manor and the cemetery are allegedly inexplicably linked by a tunnel leading from the cellar to the graveyard, possibly as an escape route for the church, or an entry point into the house used by the gentry who owned the house. The manor also overlooks Loch Ness, of Loch Ness Monster fame.

It is possible before it transferred from the local parish to private ownership that Boleskine stood as a military installation or lookout point during the rebellion years and the construction of General Wade's military road. There are many clues on its build and elevated position on the loch that indicate this.

The house was commissioned as a hunting retreat by Archibald Campbell Fraser of Lovat, whose father Simon Fraser 11th Lord Lovat ("the Fox") was the notorious Fraser who kept switching sides throughout the Jacobite uprisings, and who was later executed by beheading for treason at the Tower of London. It is said that Simon's head can be heard rolling up and down the corridor of the house.

Aleister Crowley bought Boleskine House in 1899 to seclude himself and perform magic from The Book of Sacred Magic of Abramelin the Mage, which he discovered as a member of the British secret occult society, the Hermetic Order of the Golden Dawn. It was during his time at Boleskine that Crowley became famous for his magic and occult practices, both around Scotland and around the world. Sometime during this period, Golden Dawn leader Samuel Macgregor Mathers invited Crowley to  Paris for advancement in the secret initiatory group, forcing Crowley to abandon the ritual. It is said he left without dispelling the "12 Kings and Dukes of Hell" he had summoned, and many locals blame the house's unlucky history on evil spirits left behind. Crowley himself, never one to admit a mistake, even conceded that the rituals he had performed at Boleskine House had gotten out of hand.

Many other strange tales follow Crowley's ownership. In 1965, an army major committed suicide with a shotgun only for the housekeeper to discover him moments later. 

In the 1960s, Boleskine House became one of the sites of the "Cadco Affair," also known as "the Great Sausage Scandal," a bizarre tale of how Dennis Lorraine and actor George Sanders managed to embezzle millions of pounds in government grants under the pretense of meeting a national shortage of pork products!

The next owner was another dark celebrity of a different kind–Led Zeppelin's Jimmy Page. Page spent very little time at the estate, instead bequeathing it to a friend and his family, Malcolm Dent. Dent reported strange and unexplained creaks, groans, and various ghostly apparitions, and became annoyed by the Crowley and Page fans who frequently attempted to come up to the house for a nosey.

Later owners dismissed any notions of hauntings or witchcraft at the house, but tragedy continued to strike. In 2015, the residents of the house returned from a shopping trip to find the house completely in flames. There were no injuries, as the house was empty when it ignited.

Update July 2019: The Boleskine House was recently damaged in a fire and what was left of the interior was destroyed. As of 2020, the house is enclosed in scaffolding with dangerous masonry elements around the site. All visits must be arranged with a supervising member of staff present.