I would first check that this isn’t a temporary issue.
Hotel prices and availability can vary a lot over the year. Two common cases are:
- Large events drawing a lot of people from out of town: large conventions, fairs, exhibitions, festivals or event concerts. In many cases this can completely saturate the hotel capacity in the city (and sometimes much further) for the duration of the event (from a single night to a full week or more). Prices will go up, sometimes skyrocket, or rooms will simply not be available.
- Seasons. Some cities have a peak season and an off-peak season, and prices and availability can change quite bit between the two. This is usually more for holiday destinations, but many cities will have both business and tourist visitors and of course the impact of one will end felt by the other. Sometimes just public holidays, long week-ends and the like will have a big effect as well.
Let's take one example: Las Vegas, and I picked the MGM Grand (largest hotel there, over 5000 rooms). According to Google:
- On Tuesday, November 22nd, you can get a room for €78.
- On Tuesday, December 6th, the price goes up to €2233 (no idea what event takes place at that time).
- On Thursday, January 5th, it reaches €2805 (that's during CES), 36 times more!
Las Vegas is the city with the largest hotel capacity in the world (over 150 000 rooms!), so you can imagine that if they get to this state, it's going to be much worse in smaller cities, which sometimes have events that far exceed their capacity.
In a previous life I used to often go to Baselworld, a large exhibition (over 100000 visitors from all over the world back then) in the Swiss city of Basel (which probably has hotel capacity in the thousands of rooms, maybe low tens of thousands). It's basically impossible to find a room in the city during the first few days of Baselworld (they even bring in ships to dock in the city to add more rooms), and most people will have to stay in neighbouring cities, from 30 minutes away to over an hour away! If by any chance you find anything in the city it will cost you an arm and a leg.
For those cases, just moving your trip a few days (at worst a week or two) may make all the difference between outrageous prices (or extremely low quality accommodation for a "normal" price) and a very good deal.
When it's a matter of season it's of course more difficult as you could need to move your trip quite a bit more.
You haven't told us either the destination city or the budget, so we can't tell you if your boss is really being stingy or if it's just bad timing.