Beds of Whimsy: Unusual Places to Stay in Toronto That Redefine Hospitality

Unusual Places to Stay in Toronto That Will Make Your Friends Jealous

Toronto’s unconventional accommodations market has exploded faster than real estate prices in its downtown core. These aren’t just places to sleep—they’re experiences packaged with bedding, each telling a story about the city’s past, present, and occasionally its slightly deranged architectural ambitions. From converted heritage buildings to floating hotels, Toronto offers lodgings that make conventional hotel rooms seem as exciting as tax forms.

Heritage Buildings with Modern Twists

The Broadview Hotel stands as testament to Toronto’s talent for reinvention. This red-brick Victorian beauty spent decades as Jilly’s, a strip club so notorious that taxi drivers would raise their eyebrows when you requested a drop-off. Today, at $250 per night, the only things being stripped are the bed sheets by housekeeping. Its rooftop bar offers panoramic views that make Boston’s Liberty Hotel transformation look unambitious. The 127-year-old building now houses 58 rooms where velvet headboards and record players have replaced pole dancers, though the hotel cheekily preserves nods to its risqué history.

Just west along Queen Street, the Gladstone Hotel has been welcoming guests since 1889, making it Toronto’s oldest continuously operating hotel. What sets it apart are its 37 artist-designed rooms ranging from $200-275 per night. Each room is a habitable art installation—sleep in “Canadiana” surrounded by moose motifs and plaid, or the “Teen Queen” room that looks like the bedroom of every 1990s adolescent girl’s dreams, complete with boy band posters and a vanity covered in glitter nail polish. The elevator, a hand-operated Victorian marvel, requires an operator, making it possibly the only hotel where you tip someone before even reaching your room.

For travelers with a fascination for incarceration history but without the inconvenience of actual criminal charges, The Don Jail Hostel offers accommodations in a converted Victorian-era prison. At $95 per night, guests sleep behind the original cell doors with barred windows intact. Think of it as Alcatraz, but with significantly better bedding and without the inconvenient swim to the mainland. The communal spaces occupy former exercise yards, and the breakfast room was once the prison cafeteria—though the menu has improved considerably since the days when “gruel” was the specialty of the house.

Floating Accommodations

For travelers who find solid ground too predictable, Toronto’s waterfront offers floating alternatives. Toronto Island houseboat rentals ($300-350 per night) allow guests to wake up gently bobbing on Lake Ontario with the city skyline as their alarm clock. The 15-minute ferry ride from downtown ($8.50 round trip) separates these accommodations from the urban hustle, creating an odd maritime suburb just offshore. Available May through October (because even Canadians draw the line at sleeping on frozen water), these houseboats combine the romance of nautical living with the practicality of not having to actually navigate anything.

Making Waves Boatel takes the floating concept to luxurious extremes. This stationary 65-foot yacht docked at Harbourfront offers BandB accommodations for $245 per night. The vessel features three guest cabins, each with names like “Admiral’s Quarters” that sound significantly grander than “tiny room in a boat.” Its location puts guests within a 10-minute walk of the Rogers Centre, making it perfect for baseball fans who want to combine America’s pastime with maritime sleeping arrangements. The owner, Captain Diane, serves breakfast on deck each morning, weather permitting—a meal that tastes exponentially better when consumed while watching landlubbers commute to work.

Repurposed Industrial Spaces

The Tower Automotive Building in Junction Triangle spent decades manufacturing aluminum before developers realized that hipsters would pay to sleep where factory workers once punched time cards. Now converted into lofts and short-term rentals ($275-325 per night), these accommodations feature 14-foot ceilings, factory windows large enough to accommodate actual factory equipment, and exposed ductwork that makes guests feel like they’re sleeping inside an industrial design textbook. The surrounding neighborhood, once a manufacturing district, now houses craft breweries and artisanal coffee roasters in a transformation so predictable it could be a documentary on urban gentrification.

In Queen West, The Candy Factory Lofts offer Airbnb options in the former Ce De Candy Company building, where Smarties (the Canadian version, not to be confused with the American tablet candy) once rolled off production lines. At an average of $300 per night, guests sleep in spaces where the sweet scent of sugar has been replaced by the equally intoxicating aroma of high-end design. Original brick walls, wooden beams, and freight elevators remain, while the addition of stainless steel appliances and rainfall showers ensure that guests experience industrial chic rather than actual industrial conditions. The building’s manufacturing past is preserved in details like sliding fire doors and load-bearing columns, creating spaces with more character than the entire inventory of most hotel chains.

Urban Glamping Experiences

Urban Camping Toronto has revolutionized the concept of sleeping under canvas by installing luxury tents on rooftops and in urban gardens. Available June through September for $220 per night, these aren’t the leaky, spider-filled tents from childhood nightmares. These feature actual beds, electricity, and décor that suggests someone with an Instagram following had creative input. Located primarily around Kensington Market, these tents offer proximity to Toronto’s most bohemian neighborhood without the commitment of actually living the bohemian lifestyle.

For year-round “outdoor” sleeping, glamping domes overlooking the Don Valley provide climate-controlled bubbles of luxury. Priced between $275-325 per night, these transparent geodesic structures offer the star-gazing experience of camping combined with heat, air conditioning, and beds that don’t slowly deflate throughout the night. Each dome comes with a complimentary s’mores kit, allowing guests to maintain the camping façade while enjoying amenities that would make actual campers seethe with jealousy. The domes sit just far enough from downtown to create the illusion of wilderness, yet close enough for UberEats to deliver when marshmallows alone won’t suffice.

Pod and Capsule Hotels

The Pod Hotel in the Entertainment District brings Japanese-inspired sleeping cabins to Toronto at a relatively economical $120 per night. These minimalist chambers offer just enough space for a bed and a person to awkwardly change clothes while contorted like a game of human Tetris. What the rooms lack in square footage they make up for in clever design, with storage compartments that would impress NASA engineers. While New York’s micro-hotels pioneered the “closet as room” concept, The Pod Hotel adds Canadian touches like maple leaf-shaped soap and bedside outlets actually placed where humans can reach them.

For the eco-conscious traveler, Planet Traveler Hostel offers sustainable pods with a carbon footprint 75% smaller than traditional hotels. Starting at $95 per night, these accommodations are 100% powered by renewable energy—a fact that guests can mention casually to friends back home who still use plastic straws. Located just three minutes from Toronto’s famous Graffiti Alley, the hostel combines environmental responsibility with proximity to Instagram backdrops, creating the perfect storm of millennial travel priorities. The rooftop lounge offers solar-heated floors and city views, allowing guests to feel environmentally superior while still enjoying modern comforts.

Eco-Friendly Treehouses

Urban Treehouse Toronto brings childhood fantasies to life in the Beaches neighborhood, featuring suspended accommodations that hover between earth and sky. Available from April through November at $250 per night, these structures feature composting toilets and solar power that allow guests to feel virtuous about their environmental impact while still posting enviable social media content. Like Seattle’s TreeHouse Point but with Toronto’s skyline visible through the branches, these elevated dwellings offer a surprising respite from urban life despite being firmly within city limits.

The Backyard Treehouse in Leslieville represents perhaps the most unusual of the unusual places to stay in Toronto. This single-unit rental costs $300 per night and books 4-6 months in advance—longer than many engagements or presidential campaigns. Despite its rustic appearance, it offers modern amenities including WiFi fast enough to stream movies, a kitchenette, and a shower with better water pressure than most ground-level apartments. Built by a local architect as an experiment in urban density, this treehouse has become the accommodation equivalent of Beyoncé tickets—theoretically available but requiring planning, determination, and possibly divine intervention to secure.

Artist-Designed Themed Rooms

The Drake Hotel (no relation to the rapper, though he’s certainly welcome) features Artist-in-Residence rooms that undergo quarterly transformations based on installations by local creative talents. Priced between $325-450 per night depending on the artistic caliber of your particular room, these spaces function as both accommodations and temporary galleries. One quarter you might sleep surrounded by an installation exploring urban alienation; the next, beneath a ceiling covered in illuminated origami birds. The hotel maintains a rotating exhibition schedule, meaning repeat visitors never experience the same room twice—a blessing or curse depending on your attachment to predictability.

The Annex Hotel has taken the concept further by collaborating with Toronto artists to create rooms inspired by Canadian landscapes. From $225 per night, guests can sleep in spaces that interpret the Northern Ontario wilderness or Nova Scotia coastlines through design rather than taxidermy or seashell collections. Located just a 15-minute walk from the Royal Ontario Museum, The Annex offers a double dose of culture—the possibility of appreciating art without leaving your bed, and actual museums just beyond the front door. Each room comes with a guide to the artwork and artist, transforming what could be a simple overnight into an educational experience that guests can mention casually in conversation for years to come.