I decided that we both needed a night away from the kids so I set out to book a get away at a local hotel as a surprise to her. I didn't care really where the hotel was, just that it was of a certain level of quality. I first tried standard sites like kayak.com, lastminutetravel.com, travelzoo.com, hotels.com, and on and on. Those were helpful but only in setting a baseline for me. There are some of these that will give you deeper discounts if you are willing to pay for the room without knowing the exact hotel. I wasn't ready to do this though so I went on a deeper search for the best deal.
The first thing I tried was searching for sites that post discount / promo codes for hotels. This can be REALLY useful and I highly encourage it. Many hotels will send out emails to their club members with these codes that will then get posted on sites such as http://www.retailmenot.com/. I found retailmenot.com to be the best at this. Even if the hotel isn't a chain though, try typing the hotel name into google with promo or discount and see what comes up. You might have to go through a few links but you are looking for the best deal so what's a little leg work?
Next up, I found that many hotels actually have twitter accounts just for attracting customers. Search Google for your desired hotel name or chain along with "twitter" and you'll likely get a hit. Visit their twitter page and look through their posts to see if they mention any codes. Often, even if the code was posted some time ago, it will still be active.
Don't be too proud to beg as well. I found that posting a general twitter post telling the world what you are looking for will get results. In my case I posted that I was looking for a romantic get away for that Friday night and wanted someone to knock my socks off with a deal. I got direct messages from travel agents and hotels all competing for my business. I even threw out a challenge post with mentions of several area hotels I targeted and got two of them to respond that day with offers!
Once you've found the deal you want, I suggest calling the hotel as well. Tell them your situation and that you are looking for a special weekend. You might just get upgraded a room category or receive champaign in your room as a bonus.
Lastly, sign up for their rewards program. Every hotel has them and even if you never plan to stay there again, you will likely get perks for being a member. The clubs rarely (if ever) cost anything to join so there's nothing to loose. It helps to have this on your side as well before you call and try to get that extra upgrade. Hotels love their members.
Long story short, we had a great night away at a 4 star hotel with late checkout and breakfast all for under $100. Sure it took some extra work but an hour of time on the computer and phone saved me almost $100.
Sometimes the virtual world can cross over and help you in real life in ways that matter most- of course, I'm talking about my wife! Saving money was nice too.