550 Wellington St., King West Village
King West Village—one of Toronto’s hipper neighborhoods full of bars, cafés, restaurants and converted warehouse lofts—is a fitting place for the Thompson, which has the same fun spirit as the blocks surrounding it. Locals love it, and you’ll often find them using the hotel as an unofficial clubhouse, whether at the Thompson Diner (a modernized version of a classic American diner), the rooftop lounge (with gorgeous views of the skyline), or Wildflower, a sleek nightlife spot for late-night revelry. The guest rooms feel more like your coolest friend’s apartment than a hotel; they’re designed by New York firm Studio Gaia with super modern furniture and little touches like heated marble bathroom floors—a nod to Toronto winters.
118 Yorkville Ave., Yorkville
If we may be so bold: First-time visitors to Toronto should stay in Yorkville, a central, very walkable neighborhood known for some of the best shopping in the city (the famous department store Holt Renfrew is a few blocks away). It’s also home to the Hazelton, a high-end boutique hotel with seventy-seven rooms designed by superstar local design firm Yabu Pushelberg. The overall look is minimal, streamlined, modern, and big (even the smallest rooms are the size of most other hotels' suites). And don’t go looking for color—almost the entire place is in shades of gray, white, and black. Our favorite part—aside from our own goop MRKT in the lobby—is the indoor lap pool, perfect for a swim before a steam and deep-tissue massage at the spa.
The Windsor Arms
18 St. Thomas St., Yorkville
Bursting with old-world charm but stocked with modern luxuries, each of the twenty-eight suites is spacious and beautifully appointed, and you’ll also find—interestingly—a musical instrument in each one. For a real treat book into the Windsor, replete with a baby grand piano, fireplaces in the bedroom (plus one in the bathroom), and a beautiful lounge area furnished with an antique writing desk. Other amenities include a fifteen-seat screening room, a gym, and a saltwater pool and spa. The Courtyard café does a great brunch.
The Ivy at Verity
111d E. Queen St., Old Toronto
This European-style boutique hotel is smack in the middle of the city, located in what was once an 1850s chocolate factory. Incredibly intimate, the Ivy at Verity has only four unique rooms and is named for its proximity to the Verity—a private, women's-only club. The accommodations are full of personality with vintage-looking wallpaper, soaking tubs, Italian linens, and fresh floral arrangements pulled together by the hotel's own in-house florist. In terms of amenities, you'll find a member's lounge, a restaurant, and a small spa. The Ivy is really more of a romantic inn than a hotel, perfect for those looking for a supremely private stay.
The Drake Hotel
1150 W. Queen St., West Queen West
You barely have to leave the hotel bar to feel like you've had a night out on the town at this nineteen-room boutique hotel, which seems to absorb the neighborhood's buzzy vibe. Mid-century modern furnishings, a rose-petal turndown service, and, yes, even a pleasure menu put the Drake firmly in the cool category as far as hotels go. While the Drake is primarily a hotel, it operates as a type of community gathering place with its own concert venue, an extremely popular rooftop bar, an omakase-based sushi joint, and a rotating roster of art exhibits.
The Broadview Hotel
106 Broadview Ave., Riverside
In the rapidly gentrifying East End, an 1891 Romanesque revival building that until recently moonlighted as a strip club has been born again as a hip hotel. The Broadview makes the best of its location and elevation—the glass-encased rooftop bar serves up delightful small plates and strong drinks—and the city views are the main event. We love the king terrace rooms, though all of them have thoughtful touches, including a French press and a record player with a selection of vinyl. The corner suites pay cheeky homage to the Broadview’s past life as Gilly’s Strip Club, with retro-fitted, floor-to-ceiling brass poles that act as shelves. The property definitely appeals to a younger set, and there are several microbreweries and solid brunch options within striking distance.
Soho House Toronto
192 W. Adelaide St., Old Toronto
The Toronto outpost of Soho House is in a three-story, 1830s Georgian building—referred to by locals as the Bishop’s Block—and perfectly embodies the intimate, clubby vibe for which the Soho House group is best known. It's conveniently adjacent to the Shangri-La Hotel, and members can use the luxurious pool and gym facilities next door—if they can peel themselves away from the warm familiarity of the clubhouse. The interior is eclectic but sophisticated: The cool-mint drawing room is punctuated with overstuffed sofas, a roaring fireplace, and wood paneling—it's the perfect spot to tuck in for an afternoon.
188 University Ave., Old Toronto
Infused with a distinct Eastern aesthetic, the Shangri-La manages to feel personable despite its size. Located in the heart of downtown—just next door to the Toronto outpost of Soho House—you're right in the center of the city's bustle. The accommodations are classically luxurious with huge bathrooms, high thread count sheets, and floor-to-ceiling windows. A real draw is the hotel's Miraj Hammam by Caudalie spa, which fuses traditional hammam-style treatments with Caudalie's signature vinotherapy. A huge benefit of staying at the hotel is its proximity to David Chang's Momofuku empire downstairs. Choose from one of four restaurants, including Chang's signature Noodle Bar, and hit up Milk Bar Bakery for dessert.
Four Seasons Hotel Toronto
60 Yorkville Ave., Yorkville
In the heart of Toronto’s downtown district Yorkville, the fifty-five-story property has incredible city views from every floor. The rooms are fittingly luxe and modern, done up in a tonal grey palette. Chef Daniel Boulud’s on-site French brasserie-style restaurant is an added bonus for the weary traveler who doesn't want to venture out for a good meal.