absolutely, there are numerous well managed vacation communities in the Berkshies, located usualy near skiing, ofierring a lake, pool, gym and some time even the club-house. The prices vary depending on the house, but without the doubt, under 500K can be found.
Also, you will find a charming lake in the midst of practicaly every Berkshire town, so it'll eventualy depends on the house, that will best suit your needs.
Call or e-mail me directly with your criteria, I'll send you my picks of the available homes for start, and we can start searching together as soon as you are ready.
Looking forward to hearing from you.
Assoc. Broker, ABR
Century 21 Franklin Street