Owl Creek is near several bed and breakfasts, cabin rentals, and the Giant City State Park Lodge (actually cabins). There is also a campground in Giant City Park. A little further away, in the towns of Anna and Carbondale, there are hotels. PLEASE NOTE: Many of the roads nearby are narrow, dark, hilly, and winding, so you may prefer to stay closer to the vineyard (e.g., not in Carbondale).
In general, if you prefer hotels over bed and breakfasts, I'd suggest Giant City Lodge or Stone Creek (see below). Compared to the hotels they're generally closer, more private (cabins), and more interesting. Unlike the B&B's, the Lodge and Stone Creek have more units and thus less one-on-one with the innkeepers. If you do really prefer hotels, note that Anna is closer than Carbondale, but also much smaller. The few hotels in Anna probably aren't as nice as Carbondale (with the exception of Davie School Inn, a nice bed and breakfast in Anna), and there are not nearly as many restaurant options in Anna.
These places are near Owl Creek and listed more or less by distance from Owl Creek, starting with the closest. (We've never stayed at any of them.)
Here's a map, with all these places marked, along with Owl Creek. The blue pins are campgrounds, the red are other lodging.
The Shawnee Hills Bed and Breakfast is the next closest place, and is also less than five minutes from Owl Creek, still on Water Valley Rd, but in the other direction (towards Cobden and right near Highway 51). This place has 3 rooms that are booked separately ("antique furnished guest rooms with private baths, private decks and a hot tub. A gourmet breakfast is served."). There is also a large barn where they sell antiques. There is a really awesome cave on this property ("Rich's Cave") where Daniel Boone supposedly carved his name in 1766 (you have to ask permission).
Cypress Grove Lodge is a 4 bedroom house very near Owl Creek. When their kids were grown, the couple who owns it moved and now rent it out. It has a hot tub and deck. It would be spacious, inexpensive, and pretty private option for a group of 6-8, but it's certainly not fancy.
Bruce Goff Castle is 4 miles/10 minutes from Owl Creek, by the small back roads (can go on Hwy 51, slightly greater distance and less time). Innkeeper stays in one of the towers, and sounds like they rent to only one group/couple at a time, for the whole weekend. You can pay for the use of one ($135 per night or $250 for 2 nights) or two master suites ($230/$420), or the suites plus an additional futon bedroom ($315/$570). This is a really awesome property, and it's near the winery, and I'm not sure who the innkeeper is or how he interacts with guests.
I know less about Windy Hill Acre Inn, and their website is skimpy. But they do represent another, slightly different option that's still very close to Owl Creek. It's on the same road, but on the other side of Hwy 51 and just outside Cobden. I could try to find out more if anyone is interested. I think the owners may live on site. It's between the previous two in terms of size - it's also a whole house, but with only 2 bedrooms.
Bell Hill Bed and Breakfast which is basically across the street from Windy Hill Acre Inn. Looks very nice, but is relatively expensive. It is a really neat old mansion though, if you want to splurge a little. I have not been there since it was made into a B&B - but when I was growing up, a very elderly lady lived here (Alice Fly) and she hosted a huge Easter egg hunt on the grounds each year.
Rustle Hill Winery has 2 cabins. It is 5 miles/10 minutes from Owl Creek (or 3.5 miles/7 minutes via the shortcut route...). Looks like one cabin is already booked for Memorial Day. Each cabin designed for one couple, they say can accommodate 4-6 people. This winery is pretty new - I haven't been there.
Giant City Lodge is part of Giant City State Park, but managed as a concession. It is 5 miles/15 minutes from Owl Creek (no major roads). They have a restaurant with country-style food (famous for their family-style fried chicken and dumplings meal). They have cabins that sleep 2-4 people at three prices: $79, $99, and $139. They are a little worn down, but nice and clean. This is a pretty good option if you don't want to stay at a bed and breakfast but want to stay close.
Newly added: Makanda Inn - 5 miles / 13 minutes - looks pretty nice, probably the most "luxurious" accommodations, so more expensive (140-150/night for 2 people). They have 4 rooms. It's in a nice location - in the forest, just outside this tiny town of Makanda (has a little boardwalk where you can get sandwiches and ice cream), and about half way between Owl Creek Vineyard and Carbondale.
Giant City Campground is just a little further than the lodge. See more info under the FAQ section on the Lodge's page about the Park.
Stone Creek Golf Club and Resort is more like 8 miles/15 minutes from Owl Creek. It's between Water Valley Rd and Carbondale on Highway 51. The one bedroom cabins are $99, the two bedrooms are $129, so seems like it's a better deal for 2 bedroom. A couple years ago, one person told my mom that the cell reception was poor and the sheets and towels pretty thin, but those things may have changed (and none of the places in So. IL, that I know of, are fancy or luxurious). There's also a slight discount for golf, for people staying at the cabins (although the discount isn't much), and I think this is one of the nicer golf courses (but it's all relative...).There is also a restaurant I think. (I haven't been here, as I think it was just being developed around the time I left for college).
Little Grassy Lake Campground - There are a lot of RVs here that set up for the summer, but some sections are designated for tent camping. Not a lot of privacy, lots of kids, etc. but has a beach.
Oak Grove Cabins - about 15 minutes from Owl Creek. I haven't heard anything about this place, but found online. 3 cabins, each with 2 bedrooms and a private hot tub. One cabin is already booked for the weekend, but sounds like they are not visible from one another. Memorial Day must be booked for Friday-Sunday nights ($135/night for 2 people, $145/night for 4 people).
Tool Shed Corner B&B is pretty nearby (7miles / 20 minutes) but it's all back roads and not very close to Carbondale, where most restaurant options are (35 min or more away). I've never been there. It's a little expensive - $150/night unless staying multiple nights (then $100/night). Two private suites that share a common area with a stocked fridge, I'm guessing it may be possible to negotiate price if renting both suites.
Newly added: Back to Basics cabin - 9 miles / 22 minutes, but like Tool Shed it's all back roads, and it's not very close to Carbondale (40-45 min). I actually enjoy driving the back roads.
Kite Hill Vineyards -is northwest, somewhat closer to Carbondale, about 17 miles/ ~40 minutes.
Davie School Inn is in Anna, IL - a small town (but much larger than Cobden) that is south on the highway a short distance. About 10 miles/15-20 minutes.
These small places are west of Owl Creek. They are further away, but near Alto Pass, an interesting area (antiques, awesome scenic overlooks, near one of the better wineries in the area, etc.). But beware that the roads are very curvy and dark.
Rustic Cabins
Promising (2 cabins, each with a hot tub), but it's much farther from Owl Creek - 15 miles/25 minutes. Never been there. If you want more info on owners, etc. I can ask around.
Stable House is 12 miles/30 minutes away. I don't know much about this place either, but could get more info easily. But it's cheap for 2 couples - 2 bedrooms for $125/night, but sleeps additional people for additional $10.
Newly added: Alto Guest House - 12 miles / 28 min - outside Alto Pass on the far (west) side from Cobden and Owl Creek. $120-135/night for 4 people (extra 1-2 people is additional $10/person/night). 2 bedrooms (one queen, one is two twins) plus a loft with 2 inflatable twin mattresses. Includes kitchen and hot tub. Looks like a good deal for 4-6 people, downside is the distance to Owl Creek.
More B&Bs
Cabin By The Pond - Contact Us
Cabin on the Hill - Southern Illinois Log Cabin Rental - This place is already booked most of the weekend - except Sunday night.
Hundley House Bed & Breakfast - Rooms/Rates/Extras
Hotels
Hotels in Carbondale (Google maps)
