How I accidentally discovered how to hack hotel reservations for lower rates

With so many hotel deal sites and promotions floating around the web these days, one of the toughest parts about finding the right place to stay is figuring out how to get the absolute lowest rate possible. Some days, it starts with searching for specific dates, while on others there’s a particular area that guides my search interest. However, no matter what begins the search for the perfect hotel, the defining variable almost always comes down to price.

Fortunately, there are times in life when that Hilton HHonors membership comes in handy, and I’m able to cash in for a free night’s stay at one of their worldwide locations. The last time this happened, I decided to take full advantage and book a 5-night stay in New York City since I’d only be paying for 4 of those nights. What I didn’t realize at the time was this five-night stay would change the way I look at booking a hotel room forever.

It started with a simple question: “On which of my 5 nights at the Hilton would it make the most sense for me to use my free night?”

I assumed that, similar to most other things, buying in bulk would drive the cost per unit down. Under this reasoning, I figured it’d be best to start with my original 5-night stay and set my complimentary booking to fall on either the first or the last night so that I could maximize the consecutive number of days purchased and ultimately get a cheaper stay.

Except, while completing the booking process, I made a harmless yet telling mistake.

Rather than setting my reservation to have the first night free as I’d planned, I accidentally set it up so that my free night would be the second night of my stay. This split my reservation into three separate bookings: one for the first night, one for the free night, and another for the final three nights.

Luckily, I realized my mistake prior to entering my credit card information, and I was able to go back and change it so that the first night would be free and the next 4 nights would be lumped together. This is where I noticed a key difference: Rather than lower the overall cost of my hotel booking, my total balance actually became MORE expensive when I switched to 4 consecutive nights.

How could this be?

I was almost sure that either the system had made a mistake or maybe I was just misreading the numbers. So, I went back and set the complimentary night to be on night two again just to double check. Sure enough, the overall cost of my stay went back down.

Then, I tried it again except this time I set night three to be free instead of night two splitting my stay into two 2-night stays. This time the price went back up slightly, but was still cheaper than my original 4-night stay.

I continued this process until I determined that by using my complimentary night on the fourth night of my 5 night stay, I would get the cheapest possible rate for the duration of my time in NYC.

Once I noticed this, the first thing I did was immediately complete my booking as two different reservations using this combination, as I still halfway believed there must be some glitch in the system and I wanted to take advantage of it before things switched back to normal.

However, upon securing my reservation, I began doing some research into how hotel bookings work to see if this was a process I could continue to replicate. As it turns out, hotel pricing isn’t quite as simple as the pricing model of most other goods and by splitting a reservation into two or more separate bookings, you’ll often get a cheaper rate than if you were to lump all the nights together.