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Getting a Good Deal
For US trips, I highly recommend http://www.hotwire.com/ for accommodation deals.

It's especially useful for off-season deals for fancy hotels.

For those not familiar, it's one of those set-ups where you enter your destination (including preferred neighbourhoods) and dates and it finds accommodations for you and ranks them according to price, offer and star system (or keys or whatever).

What makes it cooler than http://www.priceline.com/ is that you don't name your price, they offer and you have up to an hour to make a selection (or not). So if you're just looking, you're not locked into anything.

Once, we got St Patrick's Day weekend at the Hilton overlooking Grant Park in Chicago for US 50/night.

Other good last-minute deal: the Wyndham at Newark Airport for something like $80/night.

On the other hand, we went to New Orleans in the middle of high season this year and it couldn't do anything for us. We stayed at the Marquette House Hostel (a good deal since they have private rooms en suite with toaster ovens and fridges).

I got a really nice business hotel in Costa Mesa for $50 a night, which is about what you pay at a Motel 6.

I've had good prices when I didn't have to stay in a very specific area have also used Hotwire for airline tickets and was very pleased.

Using http://www.expedia.com/ we've gotten Wyndham Summerfield Suites for $50 in Denver and Chicago. If you like Wyndham, check their web rates. I got a room in CO Springs for $40 night, and have never paid more than $70 for a Wyndham using their Web Rates. They also give you 500 Frequent Flier Miles every time you stay if you sign up for their By Request program. (Which is nice, you get a bottle of wine and snacks in your room upon check in).

Expedia is good, but sometimes check the hotel's website directly.  It may be a few bucks cheaper.