How to gift a $ paid room?
 

For her birthday my sister asked for a room in NYC for a weekend night because she knows I have like a million points and I've gifted many award nights before. The problem is I can't make myself burn 50k points when the weekend rates are so cheap ($110 AAArate). So what's the best way to do it?

I could either reserve thru my account, or just reserve under her name with no hhonors account, but held with my CC. I know that if done thru my account she would not get my diamond benefits, but she might get some consideration on room selection since I'm the one paying. But also in either case I don't know how I could get the hotel to charge my card without me presenting it in person.

Any ideas on how to do this?

You could pay for the room upfront, non-refundable rate. Just a thought.

Put Both names on reservation
 

Do the prepaid room, put both your name and the other party's name on the reservation.

Then the other party can check in and provide a CC for incidentals.

If the front desk asks, you are coming in on a later flight.

HTH

Book it like you normally would under your account. Once booked call the diamond desk and have them add your sisters name to the reservation.

By doing it that way it will show up as a stay under your status so when she checks in there will be the upgrade and breakfast vouchers. You shouldn't get points however hilton has been known to goof and give them anyhow.

I've used this strategy for family a number of times over the years and it has always worked for me (the free breakfast and room upgrade for non-hhonors family members). I usually don't get points for the stay (since I'm not there) however every once and a while they will actually post points to my account (clearly an error on hiltons part... I always prepay the room and have family put their credit card down for incidentals).

You're saying that when you've done this your family member admits at check in that you're not coming, but they still give him the breakfast vouchers etc? I've always thought that if you did it this way they would make more of an issue that the diamond member wasn't showing up.

Just give her the $110? Seems the easiest to me. Or a Hilton Gift card

http://hhonors3.hilton.com/en/gift-card/index.html

I would not count on her getting any of your benefits if you are not staying there. It may happen in some hotels, but the rules are fairly clear on the fact that benefits are for the member staying in the room

With their name on the reservation they can check-in... you can take it from there...

Yes and then people start getting upset when the program changes and starts offers less in terms of perks. But hey, if you game the system then don't be surprised when the system changes for the worse.