If you have the right property there shouldn't be a problem. You obviously aren't going to have a wedding for 100 people at a 2 bedroom summer camp. There are some very large and private properties that I'm sure would be able to handle a crowd this size for a day. A friend of mine rents a waterfront house every season that's about 4000 sq ft and sleeps 4 families, a total of 20 people. It's owned by a bunch of investors. If you're renting out a house this size you're probable renting from a professional landlord and they will have all the paperwork and insurance issues ready. The majority of people that have a house like that are very wealthy and wouldn't rent them out.
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