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We sort a caravan that would suit are two and they always try out any cars we buy too, not much point having them if you make them unhappy leaving them behind or forcing them into a car they don't like.
We (an ex husband and I) used to have a canal boat and always took the dog - she used to love it too, especially drinking the canal water and nicking fisherman's butties
Not sure she would've liked staying in an hotel though
I have only been away for a few days 2 years ago, but the dogs came with me. I can't imagine I'd ever kennel them just so I could clear off on holiday.
I'd only worry about them so it would spoil my time away.
There are thousands of pet friendly holidays available now anyway.