We’ve been doing annual trips for 35 years and have never missed a year (even Covid where we hunkered down in our rental house and Instacarted everything) For the first 6 or 7 years we’d meet at one of our group’s lake house for the weekend, until they sold it. Since then we’ve done NYC, Boston, Cape Cod, Las Vegas, a cruise, West Palm Beach, our college town, the Finger Lakes, Charleston, Lake Lure NC, St. Michael’s MD, Atlantic City, Hilton Head, Nashville, Saratoga Springs NY, Orange Beach AL and this year is Lake George NY.
We divide the cost evenly, no matter who gets what room. The cost also includes food, beverages and usually one dinner out for the group. When times were simpler, we usually had enough money left over to go bar hopping but post Covid, that hasn’t been the case. Everyone also pays on their own for activities we decide to do.
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We tend to stay in hotels and everyone gets their own rooms. So much easier and we can meet up in the lobby, by the pool, etc. I also like having my own space and some privacy.
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And it gets easier and easier now that you can text between rooms. But on one trip I wished we had all still been in shared apartment when we switched to hotel rooms. It was nice to have privacy, but oops - we set our alarm wrong… had the other two couples waiting for us in the lobby. When they called, we sent them on their way and met up a little later.
I think it’s a fine idea to charge different prices for different rooms, but when we travel with family, we all pay the same amount. We do per person, and so the one single person winds up paying 1/2 as much, even though she obviously takes up a room.
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Interesting topic.
When we travel with kids, we usually get a place with two bedrooms and two bathrooms. The kids are ok sharing as long as there are two twin beds.
When we travel with friends, I am usually the travel arranger. I find the house to rent - we split the cost. One of our friends will always pick the “best” room - while that can be a bit annoying, I’ve let it go (he’s the oldest in our group). We split the cost of the house evenly.
I’ve been on several trips with my girlfriends. Usually rent a place with enough bedrooms and multiple bathrooms. Split the cost evenly. One friend has to have a single - so we let her have her own bedroom. I am ok sharing - another friend and I have often paired up at these trips and are very comfortable sharing a bedroom/bed.
For larger groups like our girls’ trips, a shared house just works out so much better than hotels.
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We did Passover in a set of rental properties - we gave the fanciest room to my dad because he is senior ranking plus was paying the lion’s share. DH and I took a far away room in a different building but we had our own laundry and bathroom so I thought it was win-win even though it was less “luxurious” than any of my sisters got.
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We stayed in the pink room here and it was a lovely little hotel:
Not in the midst of the Il Duomo square, but walkable for us and quite close to the train station which was what we wanted since my sister brought too much luggage. 
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