My family usually just pays someone to stay at the house w/ the dog(s).
It's actually cheaper than a kennel, your pet is in the comfort of your home, you don't have to adjust your travel plans to coordinate w/ kennel hours, you don't have to worry about your home being an unoccupied invitation to burglars, and you also don't have to arrange for mail/newspaper pickup.
I've thought about having a pet sitter. But what if s/he accidentally lets the dog out into an unfenced area and the dog runs off and gets hit by a car? Or what if s/he lets the dog out on the patio, doesn't keep an eye on the dog, a deer or another dog walks through the backyard, and my dog gets excited and jumps over the wall and runs off (she's capable of jumping over the wall -- she just doesn't know it -- that's why I don't let her out of my sight when she's out on the patio)? I also worry about the person forgetting to turn on the burglar alarm, or talking to someone about whose dog s/he is keeping and some criminal overhearing the conversation and breaking into our house. That's how our last break-in happened -- someone overheard a conversation that one of my colleagues was having about us being out of a town, and that person and her husband broke into our house. One of the disadvantages of a small town -- you lose your anonymity.
So that's why we don't go anywhere we can take our dog. I don't want her at a kennel, and I don't trust anyone except my husband to watch her as carefully as I do.
While on the subject of pets, our daughter got a cat without our permission. She knows I despise cats. They creep me out the way they get on kitchen counters and dining tables -- gross. She wants to come home for a few days and bring the cat.
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I'm afraid our dog and her cat won't get along. How likely is it that they will get along? We've always had dogs, so I dunno.