Cool Hotels Toronto: Bet On It

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The “Cool Hotels” series makes a trip north of the border to Toronto this week, just in time for some of the most celebrated races of Woodbine’s meet. In addition to the equine talent on the track, Toronto is also host of the world’s most ethnically diverse population. As a result, the location has a little something for everyone. Hopefully this list of local hotels does too!

Win: Windsor Arms
The Rate: $326 USD
The Lowdown: Rundown and left for dead in 1991, no one could have imagined the rooms would one day be fit for the likes of Tina Turner, Britney Spears, and Woody Allen. A full rehab in the late 90’s rendered a hotel that fuses the old-world charm of Toronto with modern decadence. The neo-gothic structure has nods to tradition and timeless class, both in feature and function.
Their high tea ceremony is accented with the encouragement to wear a fancy hat for the occasion, making that race day fascinator or fedora suddenly dual purpose for the weekend. Looking to unwind a little more? The Living Room features an astounding— for a hotel — number of craft drafts. 60! If retail is more your thing, Winsor Arms, is located in the luxury district, meaning Prada, Gucci, and Chanel are all within a short walking distance.  
In sum, the venue is ravishing.

Place: Gladstone
The Rate: $225 USD
The Lowdown: If you’ve ever dreamt of spending the night in an art exhibit, the Gladstone is your option to make that a reality. Thirty-seven artist-designed rooms, each unique in theme, make this hotel the antithesis of the cookie-cutter chains we have become accustomed to. My personal favorite themes: The “Teen Queen” and the “Surreal Gourmet,” which comes complete with faux marshmallow bag pillows. 
The management prides itself on a keen sense of hyper-locality that keeps the Toronto business community thriving. They offer complimentary Toronto-designed-and-built bikes to tour the city on, with the hope that on your adventure, you support a local business or two.

Show: Woodbine
The Rate: $81
The Lowdown: Location. Location. Location. Let’s face it, you came to town to be at the track! Located just a few furlongs from the racecourse, you’ll save plenty of time, money, and effort by opting for this spot. 
It’s not technically affiliated with the racing industry in any formal capacity, but you can bet on the fact you’ll be sharing the breakfast buffet with plenty of railbirds. So if you’re willing to sacrifice luxury for a bigger bankroll for the Woodbine Mile, this is an easy choice to do so.