The Best Time to Book a Hotel for Secretly Cheap Deals

Yes, there is a best time to book a hotel room, but the tricky part is that it depends on your vacation destination. For some U.S. locations, plan too far ahead and you'll pay significantly more than if you procrastinated. For other places, waiting until the last minute may backfire spectacularly.

We enlisted a travel expert to help you navigate the sometimes confusing hotel-booking game. If you're planning a getaway, read on to find out if you should book early or wait to get the best deal. And if you're not a planner, our expert has suggestions on destinations where spontaneous travelers are rewarded with lower hotel prices.

When to Delay Booking

If your destination is one of America's biggest cities, which often have more rooms than they do visitors, it's possible to score a deal even as you drive into town. In the 2 weeks leading up to check-in, nightly hotel rates decline an average of 13% in cities like Boston, New York, San Francisco, and Chicago. "There's a much larger supply of hotel rooms," travel expert Adit Damodaran explains. "If they're not filled by the weekend, hotels will offer last-minute deals."

Here are a few examples of how last-minute booking in big cities can reap savings:

• In Chicago, you can expect to pay an average of $150 a night if you book 40 days out. Wait until the week before a trip, and that figure drops to around $125 a night.
• In Boston, booking 6 months early can mean paying more than $250 a night. Book a week ahead of travel, and expect to face a more reasonable $150-per-night bill.
• In New York, early birds booking 6 months ahead can expect to pay almost $100 a night more than their procrastinating counterparts who wait until the days leading up to a trip.

When to Book Early

"If you're headed to a getaway vacation destination, those hotel rooms start to get very expensive last-minute," says Damodaran. For stays at popular U.S. vacation destinations like Miami, Hopper recommends booking hotel rooms 2 to 3 months in advance. If you're heading to Miami on a shorter lead time, Damodaran suggests looking for options further from the beach. "You'll find better availability and better prices inland," he says.

Still, even a last-minute hotel room in Miami—a city with a large number and variety of hotels—will be less expensive than a last-minute booking in Sedona, Arizona. "It's such a popular leisure destination with a very limited supply," Damodaran says of the gorgeous desert town. "Those hotel rooms get booked up really quickly because of low inventory, so prices are much higher for last-minute bookings."

Travelers booking a room within a week of their arrival in Sedona should expect to spend about $400 a night, based on Hopper's data, compared to an approximate $300-a-night average for a last-minute hotel booking in Miami. For travelers struggling to commit to a room months ahead of a trip, Hopper recently introduced a price freeze service that allows travelers to pay a fee to guarantee specific rates for future bookings.

Where to Go if You're a Last-Minute Traveler

Timely deals surface regularly in Orlando and Las Vegas, says Damodaran. Even at the very last minute, the average nightly hotel rate in Las Vegas is under $150, according to Hopper's data. In Orlando, you can expect to spend about $100 a night for a last-minute hotel booking.