pjpink – having lived in richmond for 7 years, I lost something of my tolerance for cold weather, so not sure what your tolerance is, but if you are planning a trip i'd suggest may – october in terms of nice weather. Spring is wonderful and September or October are generally beautiful crisp weather.

boston's subway system (the MTA or "T" is pretty extensive and runs from downtown, over into cambridge and out into the western portions of Boston & Brookline. I just took a look at hotels on sidestep.com and saw some good rates on boutique hotels like this one http://www.onyxhotel.com/ but haven't stayed in many hotels here don't have much to say …

That said, stay in better areas like Downtown, Financial District, Back Bay, Brookline, etc but stay out of close-by towns like somerville, medford, allston & brighton which are a little sketchier. Take a look at the hotel pictures or whatever and check it against this google mashup of t stations .. should give you a sense of where you need to stay.

http://www.thrall.net/maps/mbta.html

I will say that the Holiday Inn in Brookline is nice (but can be expensive) but has great access to many areas of the city and that if you are looking to get fancy Jury's is excellent.