We are planning a Columbus day weekend wedding as well. We booked hotel room blocks already, and got great rates -- $300-ish per night ... If your guests wait, they will pay $400-$500 a night.

So basically as long as we're planning and making appropriate reservations far enough in advance, it should be ok, right? I booked hotel rooms already and also got really great rates. I'm just worried about people having trouble with rental cars and/or plane tickets if they wait too long. And also, some people really don't like giving up their long-weekends. But so many of our guests are coming in from the west coast that we figured having an extra day would be really valuable.

I think you'll be OK so long as (1) there are no parents' weekends on C Day w/e 09; (2) no primary football match ups (i.e., Harvard/Yale, BC/Norte Dame, etc), or (3) major Boston-based events (i.e., Head of the Charles regatta, anything that will close down Mem Drive or make Storrow or Mass Ave a head ache.)

We are holding our wedding this year (/08) on Columbus Day Saturday and have been planning since last December. Consider booking hotel blocks in the 'burbs or Cambridge for great rates, good hotels, and free parking. Most out of towners will drive anyway. Good luck!