Going to Boston in a few weeks and wondering where to stay. It is the Head of the Charles regatta weekend so hotel prices are $$$$$$. Any suggestions on a great place to stay within a 20 minute drive of Boston? A suburb / outlying area that is not just sprawl and box stores, but has some character, restaurant, nice area to walk?

You could try ALOFT in Lexington. I grew up in Lexington, which is itself a tourist destination and next to historic Concord, so it has some appeal for people from out of town. You'd be about a 20 minute drive from downtown Boston, a little less to Harvard Square/Cambridge.

you could go north along the coastline - the gloucester area. it would be a little bit of a drive into the city but gloucester will be a nice quiet beach town this time of year.

Is the Marriott Courtyard in Brookline full? It's a great neighborhood, with easy access to the T.

There's also a Marriott in Newton, which is about 15 minutes into the city. I think that Marriott is close to the T, too, but not sure. Good luck!

You could try the Kimpton hotel in Cambridge - Hotel Marlow. I don't know if that is far enough outside of downtown Boston. We stayed a few years ago and loved it. Hint: Sign up to be a Loyalty member and you may get a room upgrade or a discounted rate. Have fun - we loved Boston!

I agree ALoft or Element in Lexington would work nicely for you. It's right off Rt 128 and a few miles from Lexington center, which is a nice cute downtown area with boutiques and independent restaurants.

The Marriott in Newton mentioned above is not immediately close to the T. It's a couple of miles from the Riverside T Station. However, it's convenient for a car as it's right by MassPike & Rt 128 junction. If you book there, be sure you ask for a room AWAY from the highways and ask for a room w/River view.

Right next door to the Riverside T station is Hotel Indigo. http://www.newtonboutiquehotel.com/ Not much to walk around that area but at least you can park your car at the hotel and take the T into town.

I suspect all the hotels in town (inclu Cambridge & Brookline) will be very expensive for that weekend.