The Carlyle, A Rosewood Hotel Rating: 4.5 Pearls
For celebrity lovers trying to avoid being plastered all over the tabloids, the Carlyle might be their best bet. Its expert discretion -- photos aren't even allowed in the restaurants when there are people present -- has earned the historic hotel its status as a vault to some of the city's biggest secrets. Even JFK and Marilyn Monroe reportedly trusted their affair to the Carlyle. And unlike other couples on this list, their notorious rendezvous was never conclusively proven.
Loews Regency Rating: 4.0 Pearls
This family friendly luxury hotel on the Upper East Side hardly seems like a place for sleazy encounters, but that didn't stop Rielle Hunter from propositioning John Edwards after spotting him at the Regency Hotel bar. Elizabeth Edwards wrote in her book, Resilience, that Rielle "wait[ed] for him outside the hotel hours later when he returned from a dinner, wait[ed] with the come-on line, 'You are so hot.'" And we all know where that led.
Gramercy Park Hotel Rating: 5.0 Pearls
What do you get when you mix celebrities and alcohol? Ill-advised hookups. And there's no hotter spot for celebrities and booze to mix than the Gramercy Park Hotel. Lance Armstrong and Ashley Olson were seen canoodling at this hotel's Rose Bar; Lindsay Lohan spent the night at the hotel with her now ex-girlfriend Samantha Ronson; and, most salaciously, Jennifer Aniston and ex-husband Brad Pitt were rumored to have met here for an intimate 1 a.m. rendezvous on the 18th-floor Roof Club. (A spokesperson for the hotel denied it -- but then again, staff at the hotel are forced to sign confidentiality agreements.)
Four Seasons New York Rating: 5.0 Pearls
Soho Grand Hotel Rating: 4.0 Pearls
Fall Out Boy bassist Pete Wentz and singer Ashlee Simpson may be married now, but a drunken outburst by Ashlee revealed that the pairing didn't start quite so innocently. Simpson reportedly screamed at Pete's confused ex Michelle Trachtenberg, "I hope you know, the whole time you were dating Pete, I was [bleep]ing him!" And where did this illicit bleeping begin? At none other than the Soho Grand Hotel, hubby Pete said on the Howard Stern Show. "It was at the Soho Grand Hotel [in New York City], and I'm looking in the mirrors, thinking, 'Oh my God, you are sleeping with the girl of your dreams, and you can watch yourself!'" he said. Hotel taste must run in the family: Ashlee's big sis, Jessica, spent some quality time at the Soho Grand with John Mayer in August 2006.