The president will spend 17 days at his private golf club in Bedminster, New Jersey, for what the White House bills as a "working vacation".
For someone who brands himself as an indefatigable worker, the nearly three-week holiday has raised a few eyebrows.
@BarackObama played golf yesterday. Now he heads to a 10 day vacation in Martha's Vineyard. Nice work ethic.
6:36 PM - Aug 15, 2011
But as critics point out, Mr Trump's 17-day holiday is nearly twice as long as the one Mr Obama took in August during his first year.
Before Mr Obama's August 2009 holiday in Martha's Vineyard, he took two other vacations that were said to entail work, including a weekend trip to Arizona and Colorado and a four-day trip to the family home in Chicago for Valentine's Day.
By comparison, Mr Trump has taken 11 such "working" vacations before this month to his properties in Palm Beach, Florida, and New Jersey. He also spent a weekend in June at the government-owned presidential retreat, Camp David, Maryland.
Mr Obama was labelled a hypocrite, too, after writing in his 2008 book The Audacity of Hope that no president should take vacations.
Mr Trump told 60 Minutes in November: "There's just so much to be done, so I don't think we'll be very big on vacations, no."
Last month, he told Republican senators to cancel their holidays until lawmakers could pass a plan to overturn the health law known as Obamacare.
The bill failed to pass the Senate, and Congress has adjourned for summer recess until 5 September.
Newsweek's cover on Thursday depicted the president lounging in a reclining chair calling him a "Lazy Boy".
"Imagine how bad he'd feel if he did any work," the magazine sniped.
The US is the only advanced nation that does not mandate paid leave, which is why the American work ethic seems a bit strange to the rest of the world. According to the Center for Economic and Policy Research, workers in most European countries are legally entitled to 20 days of holiday or more each year.
Australia and New Zealand also require employers to allow at least 20 vacation days annually, French employees get as many as 30 days off and Swedes enjoy five whole weeks of holiday.
In contrast, most Americans get only two weeks off, but some workers let that time off lapse out of fear of losing their jobs.
When they go low, we go high!
The good thing about science is that it's true whether or not you believe in it.
One, two, three, four, five. I would kick your ass. (Bill Russell)