"Sad to see the history and culture of our great country being ripped apart with the removal of our beautiful statues and monuments," Trump said in a series of tweets.
"The beauty that is being taken out of our cities, towns and parks will be greatly missed and never able to be comparably replaced.”
For many, the monuments to which Trump is referring serve as a somber reminder of America's racist past.
Earlier this week Trump appeared to equivocate between a hate rally and those protesting it, saying there were "some very fine people" among those who championed hate in Virginia.
Hundreds of white supremacists, neo-Nazis and white nationalists flocked to Charlottesville, Virginia, last weekend to protest the removal of a confederate statue from one of the city's public parks.
The hate rally erupted into a number of violent clashes with counter-protesters and hit a nadir when a car plowed into a group of anti-racist demonstrators, killing a 32-year-old woman and injuring nearly 20 other victims.
The White House said it is working to set up a time for Trump to speak with the family of Heather Heyer, the slain counter-protester.
Following the rally last weekend, roughly a dozen confederate monuments have either come down or are planned for removal.
Responding to Trump's apparent trivialization of white supremacist hate, British Prime Minister Theresa May said Wednesday she sees "no equivalence between those who propound fascist views and those who oppose them.
"It is important for all those in positions of responsibility to condemn far-right views," she said.
French President Emmanuel Macron went further saying in translated Twitter remarks he stands "at the sides of those who fight racism and xenophobia. Our joint combat, yesterday as today. #Charlottesville".
Thousands of demonstrators congregated Wednesday night in the southern city to reject the hate rally, eclipsing the white supremacist rally.
Momentum to remove the symbols of America's confederacy, which fought to retain slavery during the Civil War, has been building since 2015 when a lone gunman fatally shot nine black parishioners inside a South Carolina church, hoping to incite a race war.
Dylann Roof, who is currently awaiting the death penalty, prominently championed confederate symbols, as do many white nationalists and white supremacists, including those who went to Charlottesville.
In the time since Roof carried out his grisly crimes, at least 60 monuments have been removed or renamed, the Southern Poverty Law Center, that tracks hate crimes, said in April.