I think that the biggest obstacle people have is nerves. You are not sure what you are getting. That's one reason I would never use this for airfare, but for hotels there are reasons why I am confident in bidding blindly and taking the risk:
- You bid within a star level and are guaranteed that star level (I have been happy with 4 star hotels--nicer and newer Hiltons, Marriots etc, as well as 3 stars, which include Doubletree, some Hiltons, etc).
- You bid within a certain area of the city, so although you may be several blocks from your ideal location, you won't be across town. A few city blocks more than makes up for a couple of hundred dollars in savings.
- I have generally only bid on a one or two-night stay, so I don't have that much to lose.
- I found some experts who walked me through the process. The internet community at Better Bidding is fantastic! You can find out about the "free rebid" process which enables you to start low and re-bid often in order to get the best deal. They also have specific boards for each region, on which people post their recent winning bids (as you should do to add to the community if their tips help you). For example, I went to the Massachusetts board, and then the Priceline forum (they also have Hotwire tips), and found out that many people had won 4 star hotels in downtown Boston for $80 to $100 around that time, so I felt confident starting at $70, and using the free re-bid system to get me to $100, which was the accepted bid. The moderators there will even walk you through a bidding strategy if you ask for help in the specific state/Priceline board. I would be glad to give you specific help, too.
- I've done my research. I only bid on Priceline after I've looked at other options. If I know that the cheapest room I can get elsewhere is $300, it is worth a bit of a gamble for me to try to bid up to $175, saving 1/3 off, so I give it a try. Better Bidding also has posted lists of hotels that others have won (although this is not a comprehensive list, it gives me peace of mind to get an idea for the types of hotels and specific locations within the Priceline zones). They can be found in the states section on the front page of the forum (Here is a link to the New York list).
If you like the thrill of ebay, you'll probably like gambling on a great hotel rate as well. If you want to save money on hotels, but just reading this post has made you want to take an Alka Seltzer, I have also had great luck finding low rates on Quikbook. It is totally refundable, and unlike Travelocity and some other sites, there's no surcharge or prepayment required.
This post is already too long, and I know that there are questions I haven't addressed. If you have specific questions or concerns (or if you're a pro and have some sure-fire tips), please leave them here in the comments and I will try to answer them in the comments as well.
Tomorrow I will post two more great travel sanity-savers. You'll have to spend a few bucks for these, but maintaining sanity on the road is worth a few bucks for me.