Even if you are a serious planner, there are some travel situations that just defy advance booking. But rather than pay through the nose for a last minute hotel room, you can still use your traveler savvy to save money on your accommodation.
Unless you are trying to book a room in a specific hotel that is completely booked or trying to find a bargain room in the middle of a trade show, it is likely you will be able to get a deal on a last minute hotel booking. Hotels almost always have vacant rooms available, and they would certainly rather get a discounted price for them than let them sit vacant and be making no money at all. So, as a date gets closer, the price that hotel would be willing to accept for that room is likely to go down.
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This is, however, a bit of a gamble – you run the risk of the hotel room being scooped up by someone else who was willing to pay more than you were, or who got to it before you. It is a calculated risk, and if you are really on top of things and willing to take your second choice you can usually still get a great deal on a last minute hotel room. Websites like Priceline and Hotwire are particularly well-suited to help you play the last-minute waiting game.
Other ways to get bargains on last minute hotels include being flexible with your travel plans (this is not always possible, but if you can adjust your trip by one or two days in either direction you can sometimes take advantage of great discounts) and booking several things bundled together (package deals are especially good in the last minute category, where hotels, airlines and car rental agencies band together to try to keep seats, rooms and cars from being unsold). A few other websites that have good last minute travel deals include Booking Buddy, Site59 and Kayak.