Blumie

I grew up just outside of Boston (in Newton) and still have family in the area, including my parents, so I am in town a lot, sometimes staying in town and sometimes in the western suburbs. I almost always use hotwire to find hotels, and although using hotwire eliminates the ability to choose specific hotels, I've developed a technique that has led to a 100% success rate for both saving money and finding a decent and well located property. This same technique has served me well across the US, but I'm posting here on the New England board because this is where I've used it most.

1. Go to hotwire.com, enter you destination and desired dates. Click on "Find a hotel."
2. When hotwire returns its results, Click on the "Recommendation" box on the top of the page and tick the 90%+ box. Although I find user reviews inherently suspect, I have never had a bad experience at a hotwire property that has at least a 90% positive rating.
3. Now go to the map and click on those areas in which you're interested staying. When I want to stay in town, my preferred areas are Copley Sq.--Back Bay, and Boston Common--Theater District. I'll then add other areas if need be. Other areas that I think would be of interest to tourists are Back Bay--Fenway and Downtown Boston. I will then sort by price (low to high).

Searching for a hotel for tonight in Boston, hotwire is offering me a 4* hotel in Copley--Back Bay for $160 and a 4* boutique hotel in Copley--Back Bay for $167. In this case, I would opt for the latter, as it has a 95% positive recommendation, whereas the former has only a 90%. I also know from prior experience that the latter likely is the Leow's, and the former likely is the Sheraton, and I much prefer the Leow's. By contrast, if you book the Sheraton directly, the best rate for tonight is $295, and at the Leow's, the best rate for tonight is $299. (Hotwire adds a service fee to their quoted rates, and obviously both hotwire and the hotel sites will add taxes, but the savings still would be significant.)

These are not the only two options. If price were more important than location, I also am seeing a 2.5* hotel in the Back Bay--Fenway area for $139 with a 90% positive recommendation. It's a slightly less good location, and a 2.5* hotel rather than a 4*, but if I wanted to save the money, I'd gladly choose this so long as the positive recommendation level is at least 90%.

My best score using this technique has been the Godfrey Hotel, which I've gotten twice and which they list as a 4* boutique hotel in the Theater District.
When using this technique in the western suburbs, I've gotten the Embassy Suites in Waltham and the Indigo Hotel in Newton (near the Riverside T station) numerous times each, and been very happy with both.

I have to imagine there will be times, such as during graduation season in late May or early June, when this technique might fail you, but I've yet to experience that. It has worked for me every time. In terms of timing, I find that it's best to search for hotels 1-3 days in advance of your stay. So that may mean putting a cancelable room on hold until you are able to secure a hotwire hotel, but if my research shows that there are lots of rooms available, I don't even bother doing that.