Obama hosted about 500 guests at the 4.5-star hotel for a soiree with former President Bill Clinton and rocker Jon Bon Jovi in June as part of a trio of fundraisers in the Big Apple that brought in at least $3.6 million, based on figures provided by the Obama campaign.
Romney, along with 250 of his supporters, dropped by the luxury hotel in May for a fundraiser that brought in $5 million, according to Romney national finance chairman Spencer Zwick.
Romney's rendezvous at the Waldorf-Astoria was part of a two-day fundraising blitz that also included a multi-million-dollar dinner at the home of state senator and venture capitalist Scott Frantz in Greenwich, Conn.
The presumptive GOP nominee was in Connecticut the month before, meeting with female business leaders at an Alpha Graphics store in Hartford. The median household income of Greenwich, where Romney fundraised, was more than three times that of Hartford, where he held a campaign rally.
In a campaign cycle that is on track to obliterate spending records, both candidates have had their sights set on checkbooks so far this year. Obama, for instance, has held a record-setting 177 re-election fundraisers for his campaign and the Democratic Party during his first term. That's compared with just over a dozen public campaign rallies, speeches, and organizing events.
"That's typical of this stage," Thurber said. "This is the time to do that fundraising, to build up the coffers and then spend more time out there campaigning with 12 weeks left, eight weeks, left before the election."
While the Romney campaign is more than happy to gloat about their three-digit monthly fundraising numbers, the exact number of fundraisers the candidate attended is unknown, as the press is only invited to a handful of them and the campaign will rarely provide details for the others.
And as Obama and Democrats scrutinize Romney for transparency, his money events aren't always open to reporters either. This year Obama has attended at least 31 private fundraisers with high-dollar donors.
ABC's Emily Friedman and Devin Dwyer contributed to this report.