I travel quite a bit for work as well, so I can sympathize. I don't think speakers is the way to go however... first, hotel rooms are notoriously noisy and thin-walled. I won't want to annoy the other guests with my music. Plus the size of packing speakers would mean that I would check a bag each time, which is such a time waster... I pack carry on only for anything less than 10 days.
I would highly recommend getting a good pair of headphones and a good DAC/headphone amp instead. Better sound and much more portable.