Our team checks every hotel booking about every two weeks for rate movements, new promos etc.
Sometimes more sometimes less depending what's going on
Depending on the client we rebook at a lower price or if it is someone I know well I'll just move up their room catagory for the same'ish previously agreed price and put it down as a confirmed upgrade and wait for another upgrade at check-in. Hotels, unlike air, can be book and rebooked many many times without a fee which is why you should always book early and just see what happens. I always appreciate if clients spot a lower rate themselves and let us know.
I believe the people behind AutoSlash, who post in the car rental forums here, are working on a similar product for hotels to monitor prices
Thats a great service. OP, it might be worth switching agencies if the agent you were using didn’t monitor your reservations (and it sounds like they didn’t). I worked with an agent last year who was very hands off. They didn’t monitor my reservations, never followed up after our stays, took days to respond. They did what I asked which was to book room X for Y nights and of course at no cost to me so I couldn’t complain but I have since learned from lurking here that there are agents who are way more hands on and I’ll be switching agents for this year’s trips.
I have also also noticed that Dorchester properties seem to fluctuate wildly from day to day. They were my first choice for a Thanksgiving stay but when the rate had increased by $400 it one day and then bounced all over the next couple days I considered the booking too much work and went with a competitor.
Also, some properties already have announced their free night deals for summer 2020 but others haven’t so you might want to consider if the property is likely to release a deal later in the year.