Can You Change A Paid Hotel Stay To An Award Stay?
TPG reader Joey Tweeted me this question about hotel stays:
@thepointsguy: Can you book a cash reservation with Hyatt and then switch to points later?
The answer is technically no. As long as there is a standard room available, you can redeem your points. However, hotels often oversell rooms and even if you want to cancel your standard room reservation, there is no guarantee that it will go back into inventory, and then become available for a points redemption. It could just be reallocated to an existing reservation.
That said, although it's not supposed to happen, you can get it to work by calling the Hyatt Gold Passport desk and getting an agent who can switch the reservation for you. You can try to keep calling until you get an agent who is willing to make something work for you. I have done this before with success, though it's not guaranteed.
The same rule goes for most other chains as well, that you cannot convert a reservation from a paid stay to an award stay, even if your dates and all other information remain the same. You must just cancel and hope that the room goes back into the inventory. For instance, with Hilton I have had some success with them trying to change a paid reservation to a points reservation when I called, but I believe there was award space available when I requested the change.
Preemptive Bookings
Before you go making reservations and trying to switch them, though, keep in mind that some of the hotel chains will allow you to make a preemptive award booking even if you don't have the necessary points in your account at the time of booking, and then you just have to earn the rest of the points you would need before the reservation is canceled under their normal policies.
For example, when I called Hyatt to inquire about their policies, I was informed that as a Diamond member, if you are close to the needed points for a specific award and will earn them in time for the actual stay, Hyatt will preemptively book the award space for you, and then once you have the needed points they will deduct them. So that's one way to sort of hedge your bet.

The agent said it's on a case by case basis, meaning that if you are a Diamond member and wanted to book 4 nights at the Andaz Maui which would require 88,000 points, but you only had 5,000 points in your account, they probably wouldn't book the award for you, since you are nowhere near the needed amount of points.
On the other hand if you wanted to book one night at the Park Hyatt Chicago, which requires 22,000 points per night since it is a Category 6 property, and only had 18,000 points in your account, they would be able to book the award and then once you had earned the rest of the required points, Hyatt would deduct them at that time. You would have up until the time you'd have to cancel the reservation under normal circumstances (usually 24 hours beforehand with Hyatt) to earn those points, otherwise the reservation would be canceled.
I called some of the other chains such as Starwood and Hilton, and they don't have a formal policy in place from what the reps told me. Starwood said they can hold the award space for up to seven days but if the points aren't in there by the time the hold expires, the award will automatically cancel. Hilton said they can easily switch from a paid stay to a points stay...but only if there is award space available at the time you want to make the change.
I also called Marriott, and they said that they will allow Marriott Rewards members to book award stays even if they don't have enough points, and then just to call the reservations line once all the points post in the account, and then they can issue the award. In this case also, you have up until the cancellation deadline on the reservation (usually 6pm day of check-in) to earn those points and get the award issued, otherwise the reservation is canceled.
Since there really doesn't seem to be a formal policy in place at any of the major chains, my best advice is to call and if the agent says no, just call back a few times until you can get one who would be able to help you. Also it can't hurt to reach out to the property directly and explain your situation and see if they would be willing to work with you.
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