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Traveling in Switzerland without Hotel Reserations

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My Wife and I are planning a 15 day trip thru Switzerland in September 2015 using the Swiss Pass. For more flexible travel I would like to take a chance on finding suitable hotel (***) rooms or B&Bs after arriving in Appenzell, Pontresina, Zermatt, Lausanne or Montraux, and Luzern. Since we want to spend five nights in Wengen, we will go ahead and make reservations there. Would you consider the "flexible plan" too risky or will there be adequate opportunities for rooms in those cities? Are there city visitor centers at the train stations that can help with finding rooms?

Thanks

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