His comments, at a rally in Oregon, marks the sharpest tone Trump has used against his Democratic rival after he became the presumptive Republican presidential nominee.
This also was the first time in months when Trump, whose derogatory remarks for women have fueled his deep unpopularity among female voters, has been so direct in referring to the former president's affairs.
"She's been the total enabler. She would go after these women and destroy their lives," Trump said of Clinton.
Trump, a real estate billionaire from New York and the only candidate left in the Republican race to the White House, is likely to face Clinton, who has made New York her adopted state, in the November general elections.
At another rally in Washington, Trump continued his tirade against the Democratic frontrunner, saying "Hillary Clinton's husband abused women more than any man that we know of in the history of politics."
"Hillary hurt many women. The women that (Bill) abused. Some of those women were destroyed not by him, but by the way that Hillary Clinton treated them after everything went down," he said and claimed he respects women more than anyone else.
There was no response from the Clinton campaign, which has refused to get involved in personal allegations.
Trump's comments came as part of a defence against recent attacks from Democrats focused on his controversial comments and stances on women's issues. He has been criticised for his "demeaning" remarks against the wife of former party rival Ted Cruz and a Fox News woman anchor who questioned him sharply on his penchant for making crude remarks toward women.
Trump, a former reality star who joined politics only 10 months ago, has however defeated 16 Republican candidates - many of whom well-established governors and senators. He is now facing an open revolt from establishment Republicans.
House of Representatives Speaker Paul Ryan has said he is not ready to support Trump yet. Several former presidential candidates - including Jeb Bush and Lindsay Graham - have said they would not vote for Trump, thus raising questions over his capacity to unite the party in a crucial election year.
