Jiminy Peak is a great place for a family vacation Winter or Summer. The Summer brings warm days but not too hot as you are in the mountains. The mountain is easy to hike & the views of the Berkshire Mountains are superb; especially the views north to the Mount Greylock range. This mountain is only 20 minutes away & there are tons of trails for all levels (including the Appalachian trail) on the mountain.
There is plenty to do with the kids at the resort, with a fully stocked trout pond, a rock climbing wall, a 4 station euro bungee, laser trap shooting, mini golf & the alpine slide which is a blast - safe & fun for kids & adults. There are several pools on property that are never too crowded.
If you're into music, Tanglewood (summer home of the BSO) is 30 minutes south in Lenox. There's plenty of art & theater in Williamstown just 20 minutes north.
The area is extremely picturesque - it's a joy to ride the roads on a bike on a warm summer's day.
If the weather turns nasty there's a big mall with a multiplex movie theater about 15 minutes away in Lanesborough.
All in all - a great place.