Boasting one of the most iconic rooftop views in the city, this 58-room hotel in Riverside transformed itself in 2016 from a seedy boarding house, complete with strip club, to an upscale destination for nights out in an award-winningly preserved Romanesque building.

Equipped with a massive lounge, 19 playful hotel rooms, the popular Sky Yard rooftop patio, and one of the best restaurant burgers in the city, this Queen West hotspot checks off all the requirements for an epic night out. Oh, and it’s also home to the Drake Underground, one of the best live music venues in the city.

Built and named after the street it’s sat on since 1889, the historic Gladstone is one of the oldest and artsiest hotel buildings in the city. Renovations in the 2000s transformed this dramatic Romanesque building, which has since become the hub for interactive installations like the annual Come Up To My Room and performances at their Melody Bar.

With a discrete side entrance located in a Green P parking lot, this boutique hotel has taken over a 100-year-old building in the Annex with 24 rooms full of art by local artists. It’s also one of the most tech-savvy stays you’ll have: check-in is purely online (there’s no front desk here) and communication with staff happens mostly through text.

Goodbye Holiday Inn, hello Kimpton. This 14-storey, 188-room building is the Toronto outpost of the San Francisco-based hotel chain has taken the aging bones of the Holiday Inn and transformed it into a lush dwelling with a bike sharing program and pet-friendly policy.

Euro elegance is definitely the motif of this Montreal-based brand of hotels, with locations on Mercer Street and Maple Leaf Square. Chauffeur service and a partnership with Porter means guests should be prepared to have the best of travel accommodations covered during this luxury stay.

This brick building’s origins as home to what was once the city’s darkest jazz bar don’t go un-alluded to in the jazzy rooms of this 113-roomer. Eleven storeys are filled with rooms that mix retro and classic looks, with the ability to control lights and heating in each one. For more classic Italian vibes, hit up their lauded restaurant Constantine on the first floor.