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Dear Happy:
Actually, neither of the above, but let me explain.
If the trailer is attached to your car – whether you are towing it somewhere or it's just sitting in your driveway – it would fall under your automobile insurance, since it becomes part of the car. In that case, you would simply ask your insurance representative to add it to your auto policy. Then, as long as you carry coverage for physical damage – like collision or all-perils – any damage to the trailer would be covered under that policy.
If you do not plan to move the trailer, as you suggest, it is not necessary to insure it under your auto policy.
However, if you are using it only as a temporary holiday home and not as a year-round residence, it may be possible to extend your home policy to cover the trailer. More likely, though, you will need a special policy that covers both the trailer and its contents. Discuss your options with your insurance representative before moving – either your family OR the trailer!
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