Dog Destroyed Clothing While I was House Sitting - Will Rover pay?

Sorry, Rover's insurance doesn't cover that.

Where was the clothing? If it was in a reasonably inaccessible area, and the dog had to work to get at it, I would bring it up to the owner when going over how the stay went. Otherwise, I would just look at it as a learning experience.

This just happened to me. The pups in question had chewing issues before with household items so they also pup proofed the house. I had watched these pups several times with only a few mystery chewed household items. Unfortunately last time? I put my uggs by the door. I was giving one pup attention and the chewer snuck off and grabbed my uggs and shredded them. :( I did send a picture to the owners and they offered to pay for them. $180 and lesson learned. After that I took my shoes off outside and left them outside. The owner said their pup had chewed their shoes up in past, but hadn't done it for years so hadn't thought to warn me. I think the uggs were too much like rawhide and fluffy dog toys to resist. I only bring cheap shoes with me now.

I definitely think you should mention it to the owner and they should offer to replace/repair. I've also had some expensive headphones replaced by a chewing puppy in my home that was going through a stinker stage. She also grabbed a birthday cake off the island Small items I shrug off, but if it's more than a $35 item, I bring it up and my clients have always immediately offered to make right what their pups has destroyed.

That is tough. No matter how you handle it or don't handle it.