Booking your hotel can be complicated because there are so many different ways to do it today. In addition most will show you different prices even for the same hotel. One of my favorite ways to book hotels is last minute. It may seem like a risk but you usually find great rates when you wait. You can take this to the edge by waiting and booking the day of once you are already in town. This type of booking is not for everyone but kinda fun and exciting.
Try using Hotel Tonight they give you the option of Basic or Lux depending on how much style you have. This tool is fun when you decide not to look for a hotel until you land in a city.
Priceline is another good tool. I like to use the 'Name Your Own Price' option. It's nice because you can set the budget and never have to worry about going over. You will usually get your hotel for 50% or more off retail.
Beyond these two apps/websites I highly recommend trying your favorite hotel chain's app. They will usually have the best rates for their own hotels or price match. Plus you can rack up bonus room stays for frequent visits. Right now I have all of my hotel rewards adding to my American Airlines One World account. With this I can save up for free flights faster since flights are the most expensive part of traveling.
Another thing I make sure to do is try and roughly plan out where I want to go while I'm visiting and then search for a hotel in that radius.
I really try not to stress about a place to stay, ever. This may seem crazy but I had a homeless point before and most people would do everything in their power to secure a future place. I chose to not worry and just appreciate everything I had for as long as I have it. Worst case scenario you get a hostel for the night and bunk like you're in college again. I mean unless you are on a honeymoon you won't be staying in your room except to sleep and maybe shower so who cares.