Short answer: scan will return all matches. This doesn’t make it superior, because if you only want the first match, str.match[2] reads much nicer than str.scan[0][1].
ruby-1.9.2-p290 :002 > 'a 1-night stay, a 2-night stay'.scan(/(a )?(\d*)[- ]night/i).to_a
=> [["a ", "1"], ["a ", "2"]]
ruby-1.9.2-p290 :004 > 'a 1-night stay, a 2-night stay'.match(/(a )?(\d*)[- ]night/i).to_a
=> ["a 1-night", "a ", "1"]