Drake Hotel

If you think Toronto, you think Drake—and we’re not just talking about the Drake of Degrassi and music fame, although he does happen to be Canadian. The Drake is one of Toronto’s premier boutique hotels, offering 19 rooms, each with its own flavor. Though they may be small, the rooms are mighty, decorated in kitschy vintage hipster (sock dolls might be involved!). Originally opened in 1890, the hotel underwent renovations in 2001 and is now also home to The Drake Underground, a popular spot for indie acts and headliners, ranging from dancehall to mom-and-tot classical music sessions. The Drake also features a revolving door of art exhibitions, turning the spotlight on Canadian artists. The Drake is sort of a cultural easy-bake oven, and if you long to be a hipster Holly Hobby, you’ll love your time here hob knobbing with the movers and shakers of the city’s cultural mélange. From $199 per night