Hydrolysis of 3,4-dihydropyran In the 3,4-dihydropyran shown below will the oxygen or the pi electrons of the double bond attack the hydrogen cation during hydrolysis and why? 

This is my attempt towards a solution: The oxygen lone pair clearly can attack the hydrogen cation better than the pi electrons being a better a nucleophile, but according to my textbook (T.W.Grahams Solomons) the pi electrons of the double bond attacks, but shouldn't the oxygen atom be a better nucleophile than the pi electrons?
The functional group in question is a vinyl ether, and it is a mistake to consider these groups as isolated.  The oxygen is in conjugation with the vinyl group, meaning that resonance favors the entire system attacking.  There is no way to leverage conjugation as an energetic driving force if the oxygen attacks by itself.