I've done the baby monitor thing twice, but both cases, it was staying in a small B&B style hotel, and knew all the other guests (for weddings), so more like being downstairs in a house. i didn't feel comfortable in either case and it was more a quick bite to eat and back up again for one of DH or I.
Other hotels for weddings, I've paid for nannies/babysitters in the room, and most large hotels have a list if you ask.
For overseas holidays, I've tried to keep the DCs on British time, so eating around 6-7pm, which is 5-6pm UK time, let them stay up a little late then drinks on the balacony for me and DH, although the holiday we've just come back from, we paid for a suite so DH could have a room with lights on and watch films on his laptop while the DCs slept in the other room.
Previously, we've gone with Mark Warner, who do a 'toddler tea' at 5pm, then from 7pm - 10pm have free childcare.
The 'sleep in the buggy' thing was find until DC1 was 18months, but after that, he wouldn't do it anymore.
We think next year it'll be a self catering cottage/villa. Far easier.