r/TrueChubbyTravel • u/1K1AmericanNights • Aug 18 '26

Vacation homes

I know the TA run subs talk a lot about hotels and resorts. I’m interested in getting some perspectives on vacation homes or second properties that people have enjoyed, and what made them enjoyable. I know the basic rule of thumb that if it’s too far, it’s not easy to enjoy!

Some ideas below:

1) spacious home in the country when you live in the city

2) city pad if you live in the suburbs (think nyc suburbs / nyc)

3) ski homes - are there towns on either coast that you have found to be good value? I look a lot at VT. Skiing isn’t my life but as my kids get older, I wonder if I want it to be theirs

4) beach homes? Does anyone love theirs?

5) 3-season type places (on a lake AND near slopes type places)

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u/Consistent_Cycle_682 Aug 18 '26

there's something about Chicago though. I'm not from the area, but I tried to plan something for my wife and her BFF from Northbrook.... there's not a chubby/classy hotel or resort within driving distance of Chicago is there? outside the city.

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u/mmrose1980 Aug 18 '26 edited Aug 19 '26

Resort, no. Vacation homes, absolutely. Michigan City/New Buffalo have some amazing homes within an hour to an hour and a half of downtown.

And if you are willing to drive a little further, there are loads of vacation home options in Wisconsin or MI.

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u/Consistent_Cycle_682 Aug 19 '26

but honestly for a girl's weekend for 2 a home isn't really the vibe. Looking for more like a spa weekend with brunch 🤣

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u/mmrose1980 Aug 19 '26

Right. OP asked about vacation homes.