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Also make sure to scope out Tim Winship's Miles & Points column, which we run each week.
In it, Winship lists current credit card promotions. Making Reservations for the Wrong Hotel Travelers, beware: A misleading hotel name or location description could lead you to book an airport hotel when you think you're getting centrally located accommodations.
On the other hand, being an advanced planner can have its own disadvantages: Sure, you may want to have all of your travel ducks in a row as soon as possible, but it can actually cost you money to book your hotel room too early.
If having the best possible room is key to happy travel, then book directly through the hotel's website. : The old adage "Expect nothing and you'll never be disappointed" holds true here, but it's cold comfort when you really wanted a certain amenity.
But when those low, low OTA prices can't be beat—we know the feeling—you can always make a request for a certain type of room or location. Expecting Requests to Be Guaranteed King bed or two doubles? First, know that hotels will generally try to honor your requests.
As a general rule of thumb, booking more than 21 days ahead of your arrival date is a no-no for the most popular destinations; you'll be putting yourself at risk for jacked-up prices.
Your best bet is to start checking prices at least 40 days in advance and monitor the trend. If you want to make sure you get the lowest rate, the hotel booking site Tingo (our sister company) will automatically monitor your hotel and rebook you at the new lower rate if prices drop.