My first booking and it's house-sitting for 14 days over both Christmas and New Years. Pricing???

I usually just charge the one rate and that includes the drop ins.

FYI, Rover's system's will automatically apply your holiday rate to the entire booking if it includes a holiday date and I agree that it should, consistent with pricing in other industries.

https://support.rover.com/hc/en-us/arti…

I am glad to see that you are charging substantially more than your posted $30/night rate for house sitting. It should be considered a premium service because you are not only taking care of the client's pets but also their home. Normally house sitting should entail complete care for a 24-hour period per nightly charge. You are not precluded from leaving the home and doing walks for other clients, but the majority of your time should be there. However, there are many sitters on Rover who interpret the service differently. Some only stay at the house from, say, 7pm to 7am. But Rover's definition is 24 hours of care, the same as boarding. You are free to do as you like but the scope of your service should be in the profile.

If you want to charge a la carte for the drop-ins, that's your call. With your normal low rate for house sitting, that would certainly make sense.