You might have to get a moveable kennel and put it closer to where the family is...they like to be close to the rest of the "pack".

The other thing you could do is leave a really juicy treat inside the kennel, hang around and reward with praise, cuddles etc as soon as he steps foot inside.

BTW if he's really timid it's probably a good idea to move him away from DD. Otherwise think about what other spaces you could house him in, our little doggie has a kennel for daytime but when the weather is really bad and overnight he has a condo set up in the laundry, which is a space the kids generally don't go into. We have a plastic bed (to insulate from the cold floor) lined with a thin cushion for softness and an old 100% wool blanket from the op shop for warmth...he does love snuggling down there .