There are 9 peepholes and 1 telescope (Don't let the plural of the trophy description mislead you) in this game and are miss-able.
If you have completed the game and missed a certain peep-hole or telescope, you can replay the chapter by selecting a family member.
Follow these steps and you should earn the trophy first time.
1. Before you enter the Finch's House from the left side door, there is a "peephole" on the fence. You'll see a swing through the peephole
2. Once you have entered the Finch's House, 6 peepholes are available. 1 on the first floor (Library near the front door) and 5 on the second floor (Calvin, Gregory, Edie/Sven, Molly and Barbara.
3. Continue onto the story where you'll get out of the house and come to the families cemetery. When you see the statue of Odin Finch, go past him and turn right to where the telescope is. Zoom in to get a clear view of the Old House and hear Edith's commentary.
4. After passing through Dawn's classroom, you'll see another peephole of Milton's room.
5. With Milton's castle on your back, you'll see Lewis' "psychedelic" boat at a higher position. The trophy should be yours after looking through the final peephole.