Dilation is the enlargement of the chamber. Hypertrophy is the thickening of the walls caused by enlargement of the myocytes.
So for the left ventricle, things that cause volume overload or remodeling will cause dilation. So aortic regurgitation (volume overload) or non-ischemic cardiomyopathy (remodeling) cause LV dilation.
Left ventricular hypertrophy is caused by anything that increases afterload (or genetic conditions) like aortic stenosis or longstanding hypertension or hypertrophic cardiomyopathy. Note this should be differentiated from infiltrative conditions which do not induce myocyte hypertrophy but do induce LV thickening (Amyloidosis, Fabrys)