Holiday rentals in Anna

Ma's Cabin, Alto Pass, IL. Fine country lodging.

Cute and country remodel done in 2019. Recent new appliances, furnishings, flooring, heat & A/C, washer & dryer. Cabin is secluded and quiet plus 1/2 mile from Alto Pass Lookout Point and right in the middle of many award-winning wineries. 15 miles from Carbondale 4 miles from Giant City 30 miles from Garden of the Gods 6 lakes within 10-mile radius Hundreds of miles of hiking trails in nearby Shawnee National Forest 6 miles from Bald Knob Cross Please, no dogs! No smoking in cabin!

Historic home in Anna Jonesboro. Shawnee Forest.

Step into history at this charming two-bedroom, 1.5 bath brick home, built in 1898 in historic Jonesboro. It boasts cozy bedrooms with plush bedding and a spacious living area brimming with charm. Well insulated walls and hardwood floors pair with modern perks like an equipped kitchen, Wi-Fi, & a smart TV. Just minutes from Shawnee National Forest and Southern Illinois’ renowned wine country. Unwind and relax, the entire building is yours! You'll have 1898 reasons on why you love our building.

The Dome At Blueberry Hill

Escape to The Dome at Blueberry Hill, where comfort meets nature for a truly unforgettable glamping experience. Set on two private acres along the scenic Shawnee Hills Wine Trail and minutes from the charming village of Cobden- you’ll enjoy peaceful seclusion with easy access to local charm. The fully insulated dome offers cozy, climate-controlled comfort year-round. Sip wine under the stars or unwind in style indoors. Make lasting memories at The Dome- your luxury glamping retreat awaits.

Charming Cabin Overlooking 5 Acre Lake

This cozy, newly remodeled, and inviting cabin offers you a relaxing, serene, and tranquil setting. During your stay you will see nature at its finest. Enjoy a drink on the large deck overlooking the picturesque landscape as well as the lake. If you enjoy fishing then this stocked lake is the place for you. Feel free to fish on the bank or the dock. This cabin is part of the original homestead that was established in 1855 by Valentine Kimber. Located close to wine trails and interstate 57.

Secluded and Stunning Lodge - Hot Tub, Hiking

Hi, hello there, welcome! Bring your friends and family and get ready to relax. Our spacious lodge is the perfect getaway for those looking for some peace and privacy. Located adjacent to Ferne Clyffe State Park, you can lace up your hiking boots and wander straight onto the trails. The Southern Illinois Wine Trail and multiple state parks are a short drive away, but you'll soon find yourself back in the privacy of our 28 acre retreat. Come and enjoy all that our unique cabin has to offer!

Shawnee Hiking!Hot tub!Fire Pit!Wine Trail!

WELCOME TO LUXURY GLAMPING ON THE SHAWNEE WINE TRAIL OF BEAUTIFUL SOUTHERN ILLINOIS. You will be resting in an authentic oak timber cabin, built on the historical "Trail of Tears" in Union County - Anna, Illinois. This lodging offers the rustic appeal, a taste of Native America with the comforts of contemporary amenities including an outdoor hot tub all year long! *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #2.

Wine trail cozy cabin! Hot Tub!

Beautiful home on the wine trail. Explore the Shawnee National Forest, Little Grand Canyon and Panoma Natural Bridge. See Giant City State Park. Enjoy near by wineries/orchards Close to Cedar Lake where you can swim or fish. Then relax in the quiet, peaceful setting. This home has been completely renovated with two bedrooms both with queen beds. A full bathroom and a spacious kitchen with everything you will need! Deck over looks 20 wooded acres with a wonderful hot tub. Pet friendly

Cobden Retreat in the Woods

Eva’s Roost Retreat Cabin is located at Center For Lost Arts near Cobden, Illinois. Uniquely crafted rustic, zen-style cottage, designed to be close to the earth & nature. Extensive, curtainless windows facing the forest & pond allow for private views: sunrise, moonrise, forest & wildlife. Yoga mat, guitar & some art supplies. Personal outdoor space with firepit & comfy adirondack chairs. Entrance to wandering trails right outside your back door. Perfect place to retreat and renew.

The Farmhouse in Rhine Valley

Newly renovated Farmhouse in Alto Pass situated between Trail of Tears State Forest and just a hike or short drive away from Bald Knob Cross and wilderness. Minutes away from local wineries. Enjoy a peaceful pause from the hustle and bustle in our private little Farmhouse. Perfect for single family or small groups. Nearby venues and activities include: hiking, fishing, public hunting, wineries, restaurants, and many other local venues and events. Hunters are welcome.

Earnhart Carriage House

Standalone, 2 BR, light, airy, upstairs apartment for 4 guests. Full kitchen, coffee bar, washer/dryer. In our small village, there is a bank, post office, Dollar Store, library, gas station, and a park are within walking distance. I-57 is one mile. We live near a railroad crossing. If you are a very light sleeper, they may wake you. Each bedroom has a desk and sitting area and the bedside table lamp bases have outlets to charge your phone or tablet.

Magical Victorian near hiking / wine trail

Nook & Key 1893 is a restored Victorian with 3 bedrooms, 5 beds (sleeps 8), antique décor, outdoor lounge, screened porch, summer porch and all the modern amenities you're used to! Just 6 minutes from Shawnee National Forest and near wineries, antique markets, lakes, hiking, farms, and markets. Perfect for couples, groups, and private events. Spacious kitchen for feasts. Dog-friendly (pet fee refunded 50% upon request if no damage/hair).

Updated Farmhouse w/ King Suite

Cozy updated farmhouse near the Southern Illinois Wine Trail and Shawnee National Forest. This warm and comfortable home blends minimalist style with rustic charm and features a King Suite, family-friendly amenities, and a peaceful, rural feel—yet it's just minutes from town. Only 24 minutes from SIU Carbondale, it’s perfect for campus visits, hunters visiting during the season, wine trail adventures, or a weekend close to nature!