The Windsor Arms Hotel

Located deep in the heart of Yorkville, the Windsor Arms has been holding court since 1927 and is a true Toronto landmark—sort of.  It was designed by architect Kirk Hyslop and has been listed as a historic property by the city since 1983, but the hotel isn't just part of the city’s architectural past: the Toronto International Film Festival was founded at the Windsor Arms in 1976 and the hotel still offers a private screening room. Over the years, it's been frequented by the likes of Katharine Hepburn, Elizabeth Taylor, Woody Allen and more, as well as being featured in several movies. Eventually closing in 1991, the structure was then purchased, and demolished, in 1995. Sol Wassermuhl of Page + Steele was brought in to rebuild it, preserving many of the original characteristics like the stained glass window facing St. Thomas Street and the stone vestibule at the entrance. The new hotel, opened in 1999, included a new condo tower. Today, the Windsor Arms offers 28 unique suites from 500 to 1,500 square feet, all done in custom mahogany based on 1920s French styles. It's held on to its historic, discreet celeb-hideaway vibe, and you can still catch a whiff of its historical grandeur, even if it's only by sipping tea by the original 1927 fireplace in the hotel’s tea room. From $440 per night