Resize Rectangle HTML5 Canvas

Make sure to use some kind of threshold value to check for dragging on corners, use a closeEnough variable to hold this threshold then check corners by seeing if the absolute value of the difference between corner point and mouse point is less than the threshold. Apart from that, it is just a lot of cases to go through. Here is a jsFiddle of it

var canvas = document.getElementById('canvas'),
    ctx = canvas.getContext('2d'),
    rect = {},
    drag = false,
    mouseX, 
    mouseY,
    closeEnough = 10,
    dragTL=dragBL=dragTR=dragBR=false;

function init() {
  canvas.addEventListener('mousedown', mouseDown, false);
  canvas.addEventListener('mouseup', mouseUp, false);
  canvas.addEventListener('mousemove', mouseMove, false);
}

function mouseDown(e) {
  mouseX = e.pageX - this.offsetLeft;
  mouseY = e.pageY - this.offsetTop;

  // if there isn't a rect yet
  if(rect.w === undefined){
    rect.startX = mouseY;
    rect.startY = mouseX;
    dragBR = true;
  }

  // if there is, check which corner
  //   (if any) was clicked
  //
  // 4 cases:
  // 1. top left
  else if( checkCloseEnough(mouseX, rect.startX) && checkCloseEnough(mouseY, rect.startY) ){
    dragTL = true;
  }
  // 2. top right
  else if( checkCloseEnough(mouseX, rect.startX+rect.w) && checkCloseEnough(mouseY, rect.startY) ){
    dragTR = true;

  }
  // 3. bottom left
  else if( checkCloseEnough(mouseX, rect.startX) && checkCloseEnough(mouseY, rect.startY+rect.h) ){
    dragBL = true;

  }
  // 4. bottom right
  else if( checkCloseEnough(mouseX, rect.startX+rect.w) && checkCloseEnough(mouseY, rect.startY+rect.h) ){
    dragBR = true;

  }
  // (5.) none of them
  else {
    // handle not resizing
  }

  ctx.clearRect(0,0,canvas.width,canvas.height);
  draw();

}

function checkCloseEnough(p1, p2){
  return Math.abs(p1-p2)<closeEnough;
}
function mouseUp() {
  dragTL = dragTR = dragBL = dragBR = false;
}

function mouseMove(e) {
  mouseX = e.pageX - this.offsetLeft;
  mouseY = e.pageY - this.offsetTop;
  if(dragTL){
    rect.w += rect.startX-mouseX;
    rect.h += rect.startY-mouseY;
    rect.startX = mouseX;
    rect.startY = mouseY;
  } else if(dragTR) {
    rect.w = Math.abs(rect.startX-mouseX);
    rect.h += rect.startY-mouseY;
    rect.startY = mouseY;
  } else if(dragBL) {
    rect.w += rect.startX-mouseX;
    rect.h = Math.abs(rect.startY-mouseY);
    rect.startX = mouseX;  
  } else if(dragBR) {
    rect.w = Math.abs(rect.startX-mouseX);
    rect.h = Math.abs(rect.startY-mouseY);
  }
    ctx.clearRect(0,0,canvas.width,canvas.height);
    draw();
}

function draw() {
  ctx.fillRect(rect.startX, rect.startY, rect.w, rect.h);
}

init();

Do a handle system: when the mouse move, get the distance to each corner to get the first one that is near the cursor then save it and resize your rectangle according to it.

Here is a JSfiddle illustrating it: http://jsfiddle.net/BaliBalo/9HXMG/

function getHandle(mouse) {
    if (dist(mouse, point(rect.x, rect.y)) <= handlesSize) return 'topleft';
    if (dist(mouse, point(rect.x + rect.w, rect.y)) <= handlesSize) return 'topright';
    if (dist(mouse, point(rect.x, rect.y + rect.h)) <= handlesSize) return 'bottomleft';
    if (dist(mouse, point(rect.x + rect.w, rect.y + rect.h)) <= handlesSize) return 'bottomright';
    if (dist(mouse, point(rect.x + rect.w / 2, rect.y)) <= handlesSize) return 'top';
    if (dist(mouse, point(rect.x, rect.y + rect.h / 2)) <= handlesSize) return 'left';
    if (dist(mouse, point(rect.x + rect.w / 2, rect.y + rect.h)) <= handlesSize) return 'bottom';
    if (dist(mouse, point(rect.x + rect.w, rect.y + rect.h / 2)) <= handlesSize) return 'right';
    return false;
}