Adrian Monk (Monk)
Adrian Monk was not enthusiastic about vacationing with Sharona at a resort on Monk Season 1 Episode 9, "Mr. Monk Takes a Vacation." He gets a little more enthused when Bengy witnesses a murder and he's able to help the resort security chief investigate.
Conrad Hawkins (The Resident)
No one goes further for his patients than Conrad. He seems to never WANT to take a vacation. We're only two seasons into The Resident, but we're already wondering when this character is going to hit burnout.
Kate Beckett (Castle)
Kate Beckett has canceled her vacations before, but her honeymoon with Richard Castle takes the cake. On Castle Season 7 Episode 7, "Once Upon a Time in the West," the pair take their honeymoon undercover when they learn that a vacationer was poisoned at an Old-West style resort. Not what a honeymoon should be, dears.
Midge Maisel (The Marvelous Mrs. Maisel)
On The Marvelous Mrs. Maisel Season 2, Midge and her family go to the Catskills, but it isn't just a vacation. Susie, her manager, poses as a staff person at the hotel and begins booking Midge gigs in the area. By the end of the two month holiday, Midge delivers a series of comedy sets including one at a large hotel where her father, Abe, happens to be in the audience.
Max Goodwin (New Amsterdam)
Rather than rest while undergoing chemo, Max Goodwin walks the halls with his IV tree tethered to him. If Max Goodwin can't take a break from running a hospital to treat his cancer, then how is he going to find time to take a restorative vacation?
Rylan Givens (Justified)
Rylan Givens is a 19th-Century style lawman, but he's clearly inherited some of the 21st Century workaholism that we know today. On Justified Season 5 Episode 9, "Wrong Roads," Givens uses his vacation time to head to Tennessee to continue his investigation of Rodney Dunham.