Reference specific details and dish out compliments
OK, yes, this sounds obvious, but hear me out: if you want to get on the good side of a stranger who’s going off very little information to decide whether they should hand the keys to their castle over to you for a weekend -- you have to get personal. Make it clear you really, really care about being able to stay at their place. Reference very specific details about their space and compliment particular elements in their photos.
It’s also crucial that you don’t scan a listing and gloss over any crucial details that might ruin your chances altogether. If you need extra convincing, consider this story from NYC’s most popular Airbnb-er, who keeps a tiny detail in his listing to catch people who clearly aren’t paying attention.
Don't be afraid to haggle
Once you’ve got a nice back-and-forth conversation going with your potential host, and you have a feeling they’re going to approve your request to stay, try slipping in a line like, Your place seems incredible and I would love to stay here, but it’s just slightly out of my budget. Would you ever consider coming down in price to this price? Sure, it’s shameless, but it can’t hurt to ask.
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Joe McGauley is a senior writer for Thrillist. He'll take a windmill over a beach house or penthouse any day.