Hopefully the previous owners did not plant a tree on top of the system.
There should be no cracks in the casing should be visible and the ground should slope away from the well.
A quick check! Look in the faucet strainer... do you see grit or sand? This 'may' indicate a problem with the well screen. The pressure tank should read between 40 and 60 psi on the gauge on the tank. Running the water for a bit should not start the pump, this is set to go off once a certain pressure is reached.
Your home and cottage inspector should go over this with you during the inspection process.
OK, if this is an older cottage was there another well?
These must be decommissioned (plugged) by a licensed contractor. Ensure that the owner is asked if there is an abandoned well and if has been decommissioned.
If you have any doubt call in a certified MOE licensed contractor to review and inspect the well.