If I wanted to book a trip immediately following another trip, but had like half a day in between, would it be acceptable to run home and grab new clothes and stuff or not? The reason I ask is because I know many people like the longer sits, and that would of course make my trip longer as opposed to needing two different sitters back to back.
I think as long as you disclosed it up-front in the listing, packed in a way that meant you can do a reasonably quick drop-by, and weren’t picky about cleanliness/lived-in-ness when you dropped back in, then you can list it as one sit and sitters can choose for themselves if they want to apply or not.
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Why not?
Just be up front about it and come to a mutually agreeable plan with your sitter.
Say exactly what you want to do in your listing.
It will appeal to the sitter that would vs those that won’t.
I’ve done it as a sitter even as an overnight without any issues.
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As others say, as long as you’re upfront. We actually have a sit coming up where the owners will be back for 3 days in the middle of the sit. She was upfront about it, said we could of course stay or take the opportunity to see around a bit more, whatever we feel most comfortable with.
Some people wouldn’t do it, but as long as you’re upfront I’m sure you’ll find the right sitter.
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Oh cool ok! I wasn’t sure if it was against site rules or if that could be an option. That’s great to know. 
You are the cat mom. Make your own rules 
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I’ve got just this kind of sit coming up….
Sit lasts 8 days
The first 2 nights the couple are staying in a local hotel as they’re getting married 
The next 5 nights they’re going abroad on honeymoon.
They’ve asked if they can come back to the home to drop off their wedding clothes/suitcases and pick up their abroad suitcases/honeymoon stuff. I said yes of course…. but we plan for me to be dog walking during the changeover so that the doggie isn’t upset.
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Personally we wouldn’t mind as long as we knew about it before you/we accepted the sit, it makes everything so totally transparent then and on very friendly terms so we we’d be likely to say yes then anyway.
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No problem at all .
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We would never see this as a problem , we have kept in touch with all the people we have sat for and become good friends
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We had this scenario once. We were flying in and the hosts were flying in and out on two separate trips with up to half a day between. 3 weeks in total. They asked if it would be OK if they might return quickly to change their packing between the trips and we said no problem. Fortunately (for us!) due to flight delays they did not have time to return. 
But the point is if its discussed upfront - all OK! We would not have appreciated them just turning up unnanounced!