Hotel
Flight
Albany Airport is about an hour away from Pittsfield and generally has more flight options. It does tend to be a little more expensive. The Berkshires does not have an uber (technically there are three in the whole county last time I checked) so you may want to consider a rental car.
Flight
Bradley is another airport in the area, the drive is about an hour and a half from Pittsfield. This airport often has cheaper flights though less options. A rental car would be advised.