Reserving hotel rooms, rental cars, and other parts of a trip can be tricky when you’re looking for a great rate. If you reserve too far in advance, or too late, the rate can be much higher. It really depends on availability and the right timing.
A flexible plan can add further complications to reserving a hotel in advance. Can you accomplish your itinerary and get to the hotel? If you change plans or get delayed, getting to the hotel can be impossible.
On my trip using the All You Can Jet pass from JetBlue, I allocated a couple of days to driving around Massachusetts and Rhode Island with a rough intinerary. Since I didn’t know how far I would travel each day, and how long each place I visited would take, I looked for a hotel room late in the day for that evening when I knew better where I would be that night. As long as I had an internet connection, my iPhone gave me the lowest prices nearby.
Waiting until the evening usually worked well, except for the few times when there was a high demand that booked a hotel full.
For a rental car, I would reserve a rental car using the Hertz/JetBlue discount for the $20 a day rate that was offered to pass holders. It was often the best rate I could find. I would then check for better rates as the rental time drew closer, the day before and the day of. Using Priceline’s Name Your Own Price, I was able to score an even better deal just before I boarded a flight, only a few hours before I needed the car.
Waiting until the last minute started to become an addictive game. By risking a higher rate, I could lock in an even better rate the longer I waited. This was fun until it backfired on me a couple of times.
As I mentioned, demand is a key factor. In New York, after a major storm swept through delaying and cancelling flights to and from JFK, rental cars became a popular alternative. The longer I took looking for non-existent great rates, the more cars were rented, raising the rates even higher. Before I knew it, Hertz had no cars left.
From my experience, having a backup plan is the best. Try to get a great rate that can be cancelled without a fee. Playing the waiting game for lower rates then has little risk. If you find a better rate, cancel the higher rate. Although this can be bad for businesses that are left with inventory, competitive pricing is fair game for the consumer.
It is important to keep track of the cancellation deadlines. Some have deadlines days before the reservation, others the day of. Making sure you cancel before the deadline will avoid the nasty surprise of a cancellation fee or worse, a charge for the full reservation that was never used.