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Fairmont Royal York- Toronto, ON
Without question, Fairmont's portfolio of historic hotels is peerless. Under their management, and meticulous maintainence, the grand hotels constructed by the Canadian Pacific Railroad still shine a century after their construction. While best known for their Châteauesque stunners in scenic locations, such as Banff and Lake Louise, the railroad also constructed city hotels that were equally impressive, including Toronto's Royal York.
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Fairmont Château Laurier- Ottawa, ON
I absolutely love train travel, and am all about the idea of a string of grand hotels along railroad routes. While I'm about a century too late to take a Canadian Pacific or Grand Trunk Railway tour (although tourist segments do still exist), many of their stunning Châteauesque hotels still stand, including Ottawa's Fairmont Château Laurier.
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Rosemount Inn- Kingston, ON
Thankfully, Kingston, ON has no shortage of historic inns, because it has no shortage of visitors who want to stay in them. While the Rosemount Inn was not my first choice, it turned out to be a beautiful property, in a lovely historic neighborhood, which worked well for our stay.
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Prince of Wales Hotel- Niagara-on-the-Lake, ON
Niagara-on-the-Lake is ridiculously quaint, with all the charm that Niagara Falls is missing. While there may be no falls, there are also no casinos or tacky tourist attractions. There is however a lovely main street and plenty of historic buildings, including the Prince of Wales Hotel.
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Dorchester Hotel- Collingwood, ON
The first hotel at 172 Hurontario Street was a two story wooden structure called The Dominion, built around 1870. As wooden hotels are wont to do, it burned down in 1889. Unwilling to give up, the owner secured a $6000 mortage and built a three story brick building on the lot, fitted with every modern convenience of the time.