Boston Nesties
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Which area would you recommending staying in and why?? I've never been and actually didnt realize how many towns are on the Cape... but I just looked at a map 
Once I have my first visit to Cape Cod I'd like to visit Marthas Vineyard and Nantucket so if you have recommendations there too I'll take them.
Re: Cape Cod
Chatham - hands down one of the best towns for first time Capers.
It has the small town beach feel but there's still a lot to do there.
The Chatham Wayside Inn is nice if you'd rather go that route as opposed to renting a house
Agreed on Chatham.
I'd try to stay at least mid-cape (Yarmouth/Dennis/Hyannis) if at all possible. You can get the ferries to Nantucket and MV from Hyannis, and you're halfway to P-town, which is totally worth the trip.
We stayed at a B&B in Chatham and it wasn't pricey.