Pittsfield, in general, is the bad side of town.

I am assuming you and the missus are going to check out what the Berkshires have to offer.  There are a lot of bed and breakfast's that I would consider, over a hotel.  Lennox, Stockbridge, and Great Barrington have several nice ones.  And they are much nicer areas.

Eta- My wife just told me that Hotel On The North is "the only decent hotel in that area."  Take that for what it's worth.