House holiday rentals in Union County

Walk to Weddings-Wineries-Trails, Family Friendly

Pet Friendly Home in Downtown Alto Pass. Walk to Havisham House Weddings & Bourbon Bar in under 5 min! Perfect wedding guest base - Whole house sleeps 7, full kitchen, WiFi, washer/dryer, deck. Steps from Quetil Trail, Alto Vineyards & many Shawnee Hills Wine Trail wineries. Minutes to Little Grand Canyon, Giant City State Park & Shawnee National Forest hiking. House is professionally cleaned between stays. Central location to 11 award-winning wineries. Covered parking. Prime weekends fill fast!

4 mins to Bourbon Bar, hot tub, wine trail, views

Escape your worries in this spacious, serene retreat. Whether your exploring the local wineries, embarking on a girl’s trips, hiking scenic trails, enjoying a family vacation, or even casting a line on a fishing trip, our home is the perfect destination. After a day of adventure, unwind in the comfort of our well-appointed space. End your day by the pool, soak in the hot tub, or enjoy a campfire. Located just a short distance from Bald Knob Cross. Cameras actively recording at all times.

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.

River Run

Charming 1940s farmhouse. Updated 1 1/2 story house in a rural setting overlooking the Mighty Mississippi River, but close to the heart of Cape Girardeau. Our house has lots of room to relax with a large kitchen and sunroom. You can sit by a cozy fire pit and enjoy chilly evenings watching the beautiful sunsets. We look forward to you spending time in our neck of the woods (so to speak). We are located with in seven miles from the Isle casino, SEMO state university and a happening down town.

Victorian home on the wine trail

This family-friendly home, built in 1872, on the Shawnee Wine Trail sleeps 8 people and features a sun porch, a large deck with a built-in bar area and huge kitchen. Other highlights include: a newly remodeled kitchen, high-speed internet and a smart TV, double bunk beds, a fire pit with stacks of fire wood and nearby attractions like hiking, site-seeing and wineries. The home is steps from the Quetil Trail and half a mile from the Peachbarn Winery & Cafe. Enjoy this 2700 square ft retreat!

Twin Maples

Forget your worries in this spacious and serene space, 2 BR, 1 1/2 baths, with hot tub, pool table, large full kitchen, and outside room. The "outside room" invites you to relax under the twin maple trees and enjoy the hot tub, rocking chairs and porch swing, with a cup of coffee or a glass of wine. This property is a duplex, with no shared space. The out side room with the hot tub is completely enclosed with a privacy fence and is totally private and exclusive to this side of the duplex.

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

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.

Peacock On Poplar

Step into a storybook getaway in this beautifully restored victorian home built in 1887. With elegant antiques throughout incredibly comfortable beds, fully equipped kitchen, even though there is no conventional oven, wonderful outdoor spaces and a hot tub are just a couple of the highlights of Peacock On Poplar! Located on the Shawnee Hills Wine Trail with the Shawnee National Forest a short drive away for hiking, biking, and kayaking adventures.

The King's Quarters

The King's Quarters is centrally located on the Shawnee Hills Wine Trail and just a short drive to Giant City Park. The Quarters offers 2 bedrooms and 2 baths, full kitchen stocked with appliances and dishes, spacious living and dining rooms and a sun porch with a hot tub. The best kept secret though? Our large backyard offers the perfect escape to nature and our front porch swing is the most inviting place to relax after a long day.

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!

Spacious Rural Retreat

READ ENTIRE DESCRIPTION BEFORE BOOKING!!! Retreat in this spacious home, tucked into a quiet natural setting. The second story deck extends the full length of the front of the house, giving a lovely view of the peaceful surroundings. With no television or other technological distractions on the premises, this home is perfectly suitable for quality time with your loved ones and can accommodate large families.