I received 2 of the Hilton free weekend night certificates from the Citi card, these expire in Oct. 2013. I have a stay in Dec 2013 that I wanted to book before the rate increase comes into effect and have enough points for all but 1 night so inquired if the certificates had to be used to make a reservation in the year time frame or if the stay itself also had to be completed.

I spoke to the Hilton rep & she confirmed that the stay via the certificate has to be completed by the year expiration. She explained that a hotel gets the certificate number & puts it on file until you stay there & then it is submitted to Hilton for reimbursement to the individual hotel; she warned that if a booking is made outside of the year time frame the certificate will come up as expired & be rejected not at the time of booking, but when actually trying to use it. So all in all, I am out of luck for my Dec stay….but…

This got me thinking – could you hypothetically book a room now with the certificate (as from what she explained, there’s nothing in the system checking expiration & stopping you from making a bad booking), but then actually use the certificate you would be getting expiring in 2014 (from the citi spend) when you actually made the stay (ie. you check in, they say the cert on file is expired, you say, of sorry, they must have booked under the wrong number, this is the cert number, or something like that).

Of course this is all mere conjecture if the above would work and I wouldn’t personally want to end up getting screwed somehow