Interesting winter vacation rental for a large group outside Chicago

August 5, 2011 6:18 PM

I'm looking to rent a house or cabin on New Year's Eve and the night before for 15-20 people. It needs to be within 4 hours of Chicago, and ideally within 4 hours of Iowa City as well, though the Iowa people can probably stop over in Chicago if the place is worth the longer trip. I've found places online, but thought I'd query the hive mind to see if anyone knows of somewhere super awesome I haven't found.

We don't need beds for everyone, but more beds is better. About half the people are couples, and there are 2 babies and 1 toddler. Multiple buildings would be okay, provided they're within walking distance and we can all eat meals together in a central place.

It should be somewhat remote with few or no visible neighbors, nothing in a neighborhood. But also within a 30 minute drive of a grocery store. Wifi would be nice. Being winter, outside amenities like a lake aren't worth much.

Our budget is around $1500 for two nights, including cleaning fees, etc.

posted by scottreynen to Travel & Transportation (8 answers total)

I think this storybook castle in Mill Creek, IN looks neat. I stumbled upon it while searching airbnb and have been trying to think of an occasion to rent it ever since. At $995/night it's slightly out of your price range, but the price may be negotiable. Not very cabiny, but it looks so awesome.
posted by bonheur at 7:09 PM on August 5, 2011

Did you check out Galena IL? I haven't been there in years, but it was a really popular area for vacation homes for friends and family from Iowa. The vacation homes we stayed in were pretty much what you've described - on big lots out on the edge of town, but still close to amenities. Good cross-country skiing if there's snow, and Galena has some fun restaurants, historic downtown, etc.

Or check out Walworth County in Wisconsin - Lake Geneva, Elkhorn, etc. Some nice vacation/lake homes in that area, pretty country.
posted by hms71 at 7:39 PM on August 5, 2011

bonheur, Unfortunately the Mill Creek place also has a 3 night minimum (plus a $300 cleaning fee), so we'd be negotiating down from over twice our budget. But that's exactly the kind of place I'm looking for.

hms71, yes, my current top choices are in Galena, very similar to the place you linked. I've looked a bit in Wisconsin, but I'll go through those sites now.
posted by scottreynen at 7:58 PM on August 5, 2011

Nthing Galena....but Dubuque IA might fit your criteria as well. If you go, don't miss the aquarium.
posted by brujita at 9:38 PM on August 5, 2011

No specific places in mind, as I'm more in tune with the Northeast, but my friends and I did something similar last New Years, and (despite the current uproar about these sorts of websites) found vrbo.com to have a plethora of options within our price range, geographic location and length of stay requirements.
posted by undercoverhuwaaah at 3:24 AM on August 6, 2011

I agree with Galena or Lake Geneva.
posted by desjardins at 9:56 AM on August 6, 2011

As someone who grew up in this exact vortex, I have to also nth Galena. It's really the only place I can think of that would have something fitting for your criteria. I find it an annoying little tourist trap, but it would have the cabin and the amenities you seek.
posted by Lutoslawski at 11:12 AM on August 6, 2011

Hm, check out this place with 800 acres for $1000/weekend. Almost exactly 4 hours from Chicago, 3 from Iowa City.

This place in Portage is amazing; I wish I had an excuse to rent it. Google says exactly 4 hours from Iowa City, 3.5 from Chicago. Looks like it's worth it.
posted by desjardins at 11:27 AM on August 6, 2011