Beyond the Tower: Quirky Places to Stay in Toronto That Will Make Your Friends Jealous

Five Categories of Quirky Places to Stay in Toronto That Beat Standard Hotel Monotony

Toronto has developed a robust ecosystem of unconventional accommodations that defy the beige predictability of chain hotels. Each category offers a distinct flavor of the city’s creative spirit while providing comfortable shelter for the night. From historical conversions to floating bedrooms, these quirky places to stay in Toronto create memories that last far longer than the free continental breakfast at the Holiday Inn.

Boutique Art Hotels That Double as Galleries

The Gladstone Hotel stands as the crown jewel of Toronto’s art accommodation scene. Built in 1889 and once considered Toronto’s westernmost hotel, this Victorian building now houses 37 artist-designed rooms starting at $185/night. What makes the Gladstone special isn’t just its history, but how completely each room transforms the sleeping experience. The “Teen Queen” room might trigger nostalgia with its walls plastered in vintage teen magazine cutouts, while the “Canadiana” room embraces folksy woodsman decor that feels like sleeping in a Group of Seven painting come to life.

Unlike Brooklyn’s art hotels that often lean heavily on industrial minimalism, the Gladstone embraces both whimsy and distinctly Canadian references. Guests might find themselves sleeping beneath a canopy inspired by northern lights or surrounded by installations referencing Toronto’s multicultural neighborhoods. For the best CN Tower views, insiders request room 405, which frames the iconic structure through Victorian windows. The location puts guests within strolling distance of West Queen West, essentially Toronto’s version of Portland’s Alberta Arts District, but with more maple-infused cocktails and countless other things to do in Toronto.

Slightly further downtown, The Drake Hotel offers another artsy alternative with 19 rooms featuring rotating art installations and design flourishes like record players with curated vinyl collections. At $225/night, it’s positioned as a cultural hub as much as a place to sleep, with its own performance space hosting underground music acts nearly every night of the week. The entire first floor functions as a gallery space where guests mingle with local artists during frequent opening receptions, making it particularly appealing for trips to Toronto for singles seeking cultural connections.

Historic Buildings with Past Lives

For travelers who enjoy accommodations with intriguing backstories, Toronto offers several reimagined spaces where history seeps through renovated walls. Most notorious among these is The Don Jail Hostel, a Victorian-era prison opened in 1864 that now offers “cell rooms” starting at $75/night. While the facilities have been thoroughly modernized (the communal showers are considerably more pleasant than their 19th-century counterparts), original details like barred doors and stark stone walls remain, creating an ambiance part historic preservation, part adventurous lodging.

In the popular Distillery District, the Tank House Lofts convert former whiskey storage facilities into luxury accommodations for $250/night. Guests sleep surrounded by 150-year-old brick walls and timber beams once saturated with the aroma of aging spirits. The round windows and cylindrical architecture create spaces unlike any conventional hotel room, with surprising acoustics that sometimes amplify distant street musicians into private serenades.

Over in Leslieville, several former churches have been transformed into guest accommodations that retain their spiritual architecture while serving decidedly secular purposes. One standout property features guest rooms with original stained glass windows, peaked Gothic ceilings, and carved wooden details that once adorned altar spaces. Despite their age, these historic conversions have been fully renovated to modern safety standards, though guests should note that historic preservation sometimes trumps convenience when it comes to features like elevator access.

Floating Accommodations on Lake Ontario

Toronto’s relationship with Lake Ontario creates unique opportunities for water-loving visitors seeking quirky places to stay. “Making Waves” houseboat rentals ($225/night) docked at Harbourfront offer floating accommodations with unobstructed views of the city skyline. Think of them as Toronto’s answer to Seattle’s floating homes, but with more dramatic urban vistas and fewer rainy days. Most houseboats feature compact but fully-functional kitchens, outdoor seating areas perfect for sunset cocktails, and the gentle rocking that guarantees deep sleep for those not prone to seasickness.

For more adventurous water dwellers, Boat BnBs at Bluffer’s Park Marina ($150-$180/night) range from sleek sailboats to character-filled trawlers. These accommodations come with significant seasonal restrictions – they’re only available from May through October when Lake Ontario isn’t threatening to transform into a giant ice cube. Temperatures on the water typically run 5-10F cooler than downtown, with summer averages hovering around a comfortable 70F.

Practical-minded travelers should note that floating accommodations book up astonishingly fast, particularly for summer weekends that coincide with waterfront festivals, making advance preparation essential when planning a trip to Toronto. Reservations made at least three months in advance are strongly recommended. Budget travelers can take advantage of significant savings by booking during shoulder seasons (May and September), when rates typically drop 30-40% while temperatures remain reasonably comfortable.

Themed Rooms That Transport You

For those who find ordinary hotel rooms insufficiently theatrical, Toronto offers elaborately themed accommodations that transport guests into completely realized fantasy worlds. The Sci-Fi Loft in Kensington Market ($175/night) features a Star Wars-inspired sleeping pod, bathroom fixtures that wouldn’t look out of place on an alien spacecraft, and lighting effects that simulate various planetary atmospheres. It’s essentially an adult playground for the Comic-Con crowd, all contained within walking distance of Toronto’s most bohemian neighborhood.

The Annex neighborhood hosts the “Canadian Wilderness” suite ($200/night), which brings outdoor adventures indoors with remarkable commitment. Guests sleep in an actual tent (albeit one with a proper mattress) set up inside a climate-controlled apartment, complete with faux campfire, forest soundscape, and elaborate murals depicting Canadian wilderness scenes. The experience delivers all the Instagram potential of camping with none of the mosquitoes or potential bear encounters.

Hockey enthusiasts might gravitate toward the Hockey Hall of Fame suite at Hotel X ($325/night), which displays museum-quality memorabilia and even includes a synthetic ice shooting area where guests can practice their slap shots before bed. While Las Vegas pioneered the concept of over-the-top themed rooms, Toronto’s versions incorporate distinctly Canadian reference points that feel more personally curated than corporate-designed.

Travelers should be aware that most themed rooms operate under stricter booking policies than standard hotels, typically requiring 50% deposits and offering less flexible cancellation terms. The specialized nature of these accommodations also means they’re often managed by individuals rather than professional hotel staff, so communication about check-in procedures becomes especially important.

Eco-Friendly and Unusual Structures

Toronto’s growing environmental consciousness has spawned innovative accommodations that minimize ecological footprints while maximizing unique experiences. Evergreen Brick Works’ sustainable “tiny homes” ($165/night) offer compact but intelligently designed spaces in the Don Valley, just 10 minutes from downtown. These 200-square-foot marvels feature rainwater collection systems, solar power, and furnishings made from reclaimed materials, all without sacrificing comfort or style.

In the High Park area, several tree house accommodations ($220/night) defy expectations by fitting remarkable amenities into elevated structures. Despite their compact footprints, these arboreal retreats include features like rainfall showers, compact kitchenettes, and wraparound decks perfect for morning coffee or evening wine. Access typically involves climbing sturdy spiral staircases, making them unsuitable for those with mobility concerns but magical for the able-bodied adventurer.

Perhaps most dramatic are the glass igloo-inspired domes at Cherry Beach ($275/night), which become particularly magical during winter months. These transparent structures allow guests to stargaze from bed when temperatures hit 20F outside while remaining toasty warm inside. The juxtaposition of snowy landscapes viewed from climate-controlled comfort creates a uniquely Canadian experience that rivals Scandinavian glass igloos but with Toronto’s skyline providing additional visual interest.

Budget-conscious travelers can explore University of Toronto’s summer stay program, which offers sustainable dorms for just $65/night between May and August, perfect for those following a comprehensive Toronto itinerary on a tight budget. While less luxurious than commercial options, these accommodations provide excellent value in high-demand neighborhoods and often include access to university facilities like gyms and libraries. The concept resembles eco-retreats found in Vermont but with the metropolitan advantages of downtown Toronto just steps away.