Your long tail traffic won't be directed to your own serps... but mostly to your hotel pages. Regarding your landing pages, I would personaly suggest you think of removing the /parent (cities, for example)
Posts made by AgendizeSEO
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RE: Advice for structuring hotel websiteposted in Intermediate & Advanced SEO
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RE: Site Migration due to Corporate Acquisitionposted in Web Design
The complexity of your 301 map should not determine wether or not you should change your URL structure. It just seems like a necessity for the whole project.