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Chester Hotels Limited was a small hotel company incorporated in Nova Scotia on June 1, 1959. Victor DeBedia Oland was President of the company, Bruce S.C. Oland was Vice-President, and Don J. Oland was Secretary-Treasurer. Gordon Cowan also acted as interim President of the company. The company was formed to purchase Bryans' Villa Inn in Chester from William F. Bryans. The Inn was renamed the Sword and Anchor Inn and Forbes Thrasher, a well-known hotelier, was appointed manager. The company also ran and maintained the Sheet Anchor House, a separate lodging across the street from the Sword and Anchor Inn.
Forbes Thrasher resigned as manager in December, 1962 and became President of the Innkeepers Guild of Nova Scotia in 1963. Hugh Parker became general manager of the Inn in March, 1963 and various other managers were appointed over the years. The company experienced numerous financial hardships, often operating at a loss. In 1974, the Sword and Anchor Inn was sold to R. David Neima, President of Piper Advertising Company in Dartmouth, Nova Scotia.
Chester Hotels Limited was a wholly owned subsidiary of Keith Hall Investments, a real estate and property management company that was wholly owned by Lindwood Holdings Limited.