Talk to a local lender who can review all of your financial info. Besides down payment, you'll need a credit score of at least 620-640, a decent debt to income ratio, stable employment history & steady income, etc.... more
There are a few shops and restaurants (Stissing House is very good), but enough to do for a weekend is likely pushing it. Maybe a few hours. It's a very small town. If you have a car, you might visit Rhinebeck (shops, restaurants, and a great movie theatre) or Hudson, New York (which has tons to do).
Associate Broker, Massachusetts, New York, and Connecticut
Berkshire Property Agents
12 Railroad Street
Great Barrington, Massachusetts 01230