Does anybody know from experience how long of a drive I should allow on a Thursday morning in the 8:30 AM to 9:30 AM in August from Bennington, VT to Marlboro, VT.
Also, would you recommend staying in Bennington or somewhere closer to Marlboro based on accomodations? Ultimately our destination is Marlboro College Thursday AM at 9:30. I am driving up Wednesday later in the day from Rochester, NY and could stop for the night anywhere between Bennington to Marlboro. Any suggestions on some accomdations would be great.

Should take 45ish minutes. Give yourself a little extra time in case you get behind slow traffic (not to many places to pass).
Brattleboro is the closest "large" town to Marlboro, but since you're coming from the west Bennington is a good choice. Nice town to explore. I've never stayed at a hotel in Bennington (mom lives there), but for my sister's wedding we put up our guests at the Best Western New Englander and the Paradise. Both are nice, clean and reasonably priced.

Thanks for the quick reply and the info. I will check out both of those hotels. Would you suggest one over the other?

Well, the Paradise is right on Route 9 which is the road you'll take to Marlboro, so that may the best choice. Plus, it's set back off the road, so you shouldnt hear to much road noise.
The Best Western is located on Northshire Dr, a mile or two north of downtown. It's on a busy strip of restaurants and shopping plazas. Some of the rooms are set back off the road, while some are fairly close.
Hope this helps!

PS. The Best Western is on Northside Dr (not Northshire).

It was a great help! Paradise it is!
Have a nice weekend!
Thanks a bunch.