The Northern Irish broadcaster voiced his displeasure at a particular kind of tax – known as IR35 – which centres around the work of contractors.
During the discussion on Wednesday, the Belfast man said it was a tax many “don’t know about”.
When interviewing Shapps about how the Conservatives would fund their 2p tax cut, Holmes interrupted him and said it would be “by stealing from people”.
“I am one of them. This IR35 is one of these retrospective taxes that people don’t really understand,” he added.
“It’s going to come for you if you’re a window cleaner, a teacher or whatever.
“You guys go back and say, ‘you know we said you’re freelance, well that’s changed’. It’s stealing. It’s theft.”
“The tax was brought about by George Osborne then he sloped off as he stole money out of people’s pockets”, he added.
“It’s fine to say to people, ‘we’ve been agreeing your freelance but actually we’ve got that wrong, we’re going to change that’, I don’t think anyone has any issue with that.
“It will affect you, if you are a taxi driver, a Gardner, a painter or decorator. They put people like me in the papers because it will give them a headline and go, ‘he will be dodging his tax’, and then they will come and knock on your door and do the same.
“When I hear the Tories say they’re the party of small business, tell us, if you’re a small business, how they are helping you.”
During the discussion, Mr Shapps said he was “sorry” the Northern Irishman had been impacted by the IR35 rules.
It’s not the first time the 64-year-old has aired his grievances about the issue.
Back in January Holmes branded HM Revenue and Customs (HMRC) the “department of thievery” after discussing tax reforms on his breakfast programme.
At the start of the year the TV host revealed he had to sell his Belfast house to pay a tax bill.
In a wide-ranging and candid interview with his former UTV colleague Gerry Kelly, Holmes expressed anger at having to sell his home in the Belmont area of east Belfast and said he had lost two appeals against HMRC which cost him “hundreds of thousands of pounds in legal fees”.
The Belfast man has recently been in the headlines after it was announced he was splitting with Ruth Langsford after nearly 14 years of marriage.
Holmes and Langsford, who both formerly presented This Morning on ITV, have one son named Jack, born in 2002. They confirmed their divorce last month. Holmes also has three other children from his previous marriage.