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I have a great pet sitter who comes to our house and is also our close friend. She (Linda) also happens to be the co-author of our blog. But, as to the question of a holiday, it depends if we go out of town for it because, if we don't, then we take the dogs along everywhere we go.
One of the issues is that most hotels, even though they claim to be pet-friendly, won't accept dogs over a certain (small) size (refer to NY Times article last Sunday)