Interactive Labeling of Images

Here is a beginning :

imageList=Take[Flatten[ImagePartition[ExampleData[{"TestImage","House"}],{50,50}]],7];

Table[
   With[{i=i},
   Button[
   Dynamic[If[i===start || i===stop || (NumericQ[start] && NumericQ[stop] && start <= i <= stop), Framed[#,Background->Red], #]& @ imageList[[i]]],
   If[CurrentValue["ShiftKey"]===True,stop=i,start=i]
   ]],
{i,1,Length[imageList]}]  

Left-click on the first image of the sequence you want to select.
Shift-left-click on the last image.

The variables startand stop get the indexes of the selection.

enter image description here

Of course, you can apply Row, Column, MultiColumn... on the list of button-images above and the buttons will still work.