Coolest Neighborhoods To Stay In Toronto, Canada - Updated 2024

1. Guildwood (from USD 99)

A stone pillar and cast-iron gateway welcome you to Guildwood, one of Toronto’s most beautiful neighbourhoods. The crown jewel of Guildwood is definitely the 1914-built, historic Guild Inn, which today features a wonderful historic architectural walking tour and a rustic woodland nature trail in the overlooking Scarborough Bluffs. Guildwood is also home to some of Toronto’s oldest structures including the Guild Inn, the Osterhout Log Cabin and the Guildwood Gates. If you’re in Guildwood in June, don’t miss the Guildwood Day celebrations.

Stay on a budget at the Park Motel right next to Halbert Park, complete with internet, cable TV, and a microwave and a fridge, and even a cafe and restaurants a few minutes away.

2. Weston (from USD 137)

With the arrival of the Go Station and the UP Express, Weston has become the new ‘it’ neighbourhood everyone’s talking about. This neighbourhood possesses more of a village-like vibe due to the presence of the cool little retail and eateries strip of the main Weston Road. Weston is also home to the Artscape Weston Common, a community cultural centre, one of Toronto’s 7 Carnegie libraries, Toronto’s oldest bookstore Squibb’s, one of Toronto’s oldest farmer’s markets, parks, and even a Santa Claus parade!

With Toronto International Airport just 20 minutes from here, stay at the Holiday Inn at Toronto International Airport which means you can easily commute to Weston and the lovely neighbouring hoods.

3. Harbourfront (from USD 305)

Harbourfront is Toronto’s playground with spectacular views of Lake Ontario and is home to music, food, and cultural festivals, and tons of parks, beaches, and outdoor recreation areas. Foodies will love Harbourfront’s International Marketplace Festival and the many alfresco joints. Night owls can party at the many swanky dance clubs and rooftop lounges. Harbourfront is also home to the majestic Harbourfront Centre, where close to 4,000 arts and cultural performances take place annually.

Stay at the Aaira Suites Grand Trunk, a great modern apartment with all amenities such as smart TV, Wi-Fi, a fully equipped kitchen, and with the additional advantage of being close to all major Toronto attractions.

4. Oakwood–Vaughan

The former ‘streetcar suburb’ of Toronto Oakwood-Vaughan has transformed into an art-based, desirable neighbourhood and hub today. This largely residential neighbourhood is home to a historical Portuguese and Italian community, the legacies of which have been left behind in the form of sports bars, restaurants and cutesy bakeries. Oakwood-Vaughan is also a burgeoning arts community, housing the Oakwood Village Library and Arts Centre and playing host to the annual Oakwood Village Arts Festival.

Enjoy your stay in multicultural Oakwood-Vaughan at Toronto’s Favourite Urban B&B, where modern living and wooden flooring meets free Wi-Fi and continental breakfasts, all available at a location that’s very accessible and central.

5. Queensway

The eponymous Queensway Street lends its name to the beautiful upcoming neighbourhood of Queensway in Etobicoke. This quaint now-residential pocket is one of Toronto’s popular upcoming neighbourhoods, thanks to the announcement of the Queensway Business Improvement Area. The arterial Queensway Street is the heart of this neighbourhood, playing host to independent box stores, grocery outlets, mom and pop stores, and even hip urban speciality shops selling everything from clothes to French macaroons.

If you’re on a budget, stay at the Queensway Motel near Queensway Highway, which has simply furnished rooms, free Wi-Fi, cable TV, telephone, and is just 15 minutes from Toronto International Airport.

6. The Annex

One of Toronto’s coolest neighbourhoods is also one of its oldest and its most prominent ones. The Annex is most popular for its turn-of-the-century housing, its proximity to the University of Toronto, and a wealth of independent shops and restaurants with a Bohemian vibe. The Annex is a great, great place to hang out, what with concert venues (Dance Cave/Lee’s Palace), bookstores (BMV books), century-old movie houses (Bloor Hot Docs Cinema), kitschy, one-of-a-kind establishments (bargain shop of honest Ed’s, Annex pawn shop), and loads of cafes, pubs, and restaurants (Snakes and Lattes, Salt & Pepper Catering Co., Madison Avenue Pub).

Stay Bohemian style at the Spadina 11 Guesthouse, which is a simple but unique accommodation with modern rooms and a shared kitchen right in the heart of the Annex and close to the public library, shops, and restaurants.

7. Riverdale

Earthy, funky, eclectic - nobody can possibly resist the charm of Riverdale, one of Toronto’s biggest as well as most desirable neighbourhoods to reside in. With Lake Ontario and the Don River just a few blocks away, this diverse, trendy neighbourhood is full of community gardens, cutesy organic cafes and patisseries, and smaller communities, each with its own values and styles. Spending a lazy afternoon in Withrow Park and strolling the many Farmer’s Markets in Riverdale might be the perfect way to get a taste of the real Toronto.

What better a way to experience the history of Toronto than staying at the 19th-century-built Broadview Hotel? That and its Richardsonian Romanesque architecture are the stark opposite of the boutique hotel’s modern interiors, complete with Wi-Fi and flat-screen TVs in the 58 rooms.

8. Ledbury Park (from USD 97)

The neighbourhood of Ledbury Park in Toronto is the perfect place to live in if you prefer and like the slower life of the suburbia around you. Modernized, grander versions of post-World War II homes line perfectly perpendicular streets. Not only is Ledbury Park home to the old gem that is the Armour Heights Community Centre, but it also has the green Ledbury Park with a reflecting pool and numerous day spas and restaurants, making it the perfect place to spend a day unwinding in Toronto.

Stay right across from the popular Yorkdale Mall at the Holiday Inn which, apart from all modern amenities for adults and children, also has the added advantage of having access from both the highway and the subway. The Holiday Inn also features the Holidome equipped with billiards, ping-pong, and nerf tennis!

9. Richview (from USD 96)

If there is one Toronto neighbourhood that has the most number of lush green spaces and parks, it is Richview. With rolling, tree-lined streets, the post-World War II suburban neighbourhood of Richview is home to stunning Georgian revival bungalows and homes arranged in typical World War II-style, with cul-de-sacs and winding lanes. Once an extremely busy intersection, Richview’s leafy boulevards today also house the Richview Methodist Church, the Richview Bakery and Bistro, and tons of gardens, parks, and green spaces that are perfect for walking around at the end of a day of exploration.

Stay at the luxurious, high-rated Four Points by Sheraton located in the west-end airport district just 5 minutes outside Richview and around the same distance from Toronto International Airport.

10. Kensington Market (from USD 72)

Established by Jewish immigrants in the 1920s and now home to Vietnamese, European, Latin American, and Caribbean immigrants, the bohemian Kensington Market reflects Toronto’s wide diversity. Nestled between Little Italy and China Town, the eclectic and energetic Kensington Market features lively stalls, vintage clothing, indie, and organic boutiques and shops, art spaces, international and indie cafes and restaurants, and Victorian houses along its tree-lined boulevards.

For the best experience of staying in Kensington Market, head to the Toronto Travellers Home. With a very convenient location close to all of Toronto’s attractions including CN Tower, the Bayfront and the Distillery District, Toronto Travellers Home makes for a great affordable stay in central Toronto.

Thrilling Toronto

Bohemian, modern, homely, laidback, buzzing—Toronto and its stunning and modern neighbourhoods have a character that is unique to each of them, suiting a vast spectrum of travellers and their requirements. Choose one of these coolest neighbourhoods in Toronto, Canada to stay in during your visit to this buzzing Canadian city.