Holiday rentals in Calhoun County

Cozy Country Getaway – 3BR/2BA Home

Escape to our peaceful 3BR/2BA home in Winfield, MO! Nestled in the countryside and centrally located to Troy, Old Monroe, Moscow Mills, Elsberry & more, it’s the perfect blend of comfort and charm. Enjoy a spacious layout, fully stocked kitchen, Wi-Fi, and a big yard to relax. Great for families, couples, or weekend getaways. 40 min to St. Louis and all surrounding attractions , nature, small-town fun & more! Come unwind and make yourself at home we’d love to host you! Events must be approved

Riverfront Cabin • Deck Views + 5 Acres

Welcome to The Riverhouse – a cozy cottage retreat perched on 5 private acres overlooking the Illinois River. Unwind on the wide back deck with sweeping views of the water, or enjoy a quiet morning coffee surrounded by nature. Inside, the home is thoughtfully styled with decor inspired by the river’s charm—think fishing, boating, and the laid-back rhythm of life on the water. Perfect for a weekend escape, a peaceful solo stay, or reconnecting with friends and family just steps from the river.

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

Private cabin between Mississippi/Illinois rivers

My place is close to St.Louis. You’ll love my place because of the location, the outdoors space, the ambiance, and the tranquility. My place is good for couples, solo adventurers, business travelers, or someone wanting some privacy and looking to escape the hustle and bustle of the big city. The cabin is secluded and very private and you won’t be able to see other homes. This is not a subdivision or a neighbor hood dwelling. You are in the boonies. Our guests especially love the star gazing.

Flynn Inn

River View – Walkable to Downtown Grafton-Bike Trail located across the Street- This updated 2-bedroom, 2-bath home offers detailed finishes and a relaxing river view. With two private bedrooms, a pull-out sofa, and space for 6 guests, it’s ideal for families or friends. Enjoy the oversized soaking tub, two expansive patios, and a large screened-in porch. Just a short walk to downtown Grafton’s shops, restaurants, and riverfront, this home provides the perfect mix of comfort and convenience.

Cozy Cajun Rentals

This mobile home is in a peaceful, rural area with residential properties and natural surroundings. Foley is a small town in Lincoln County, offering a more laid-back lifestyle. The area is surrounded by farmland and wooded areas, providing opportunities for outdoor activities. Nearby amenities include parks and small shops in the town of Winfield and Elsberry, about 10 to 20 minutes away. While larger retail and dining options are Troy, O'Fallon & St. Peters Mo. are 20 to 30 minutes

70’s Park Side Cabin with Kayaks

Welcome to our renovated 1970’s park side cabin!  This cute cabin is located in Cuiver River State Park and is close by several wedding venues. The cabin is a three bedroom and two bath, which is great for family trips or just a weekend getaway. We highly suggest; hiking, biking, running, kayaking, fishing, and taking pictures in the park. Our park side cabin has a simi stocked kitchen to help ease your stay. We hope you enjoy all the improvements we have made in this unique cabin!

Grafton Getaway@Riverhouse (a waterfront property)

Our Riverhouse is one of six Grafton Getaway Guesthouses (Farm, Cabin, Lodge, Countryside, Cottage) and all have similar amenities guests love: *bicycles for guest use, BBQ grill, classic record player, 3 Smart Tv's *hammocks and swings and a putting green *complimentary coffee, tea, and hot chocolate *fire - electric, two gas pits, traditional pit with free firewood *foosball, family games, and Kids Zone outbuilding *free 50 meg WiFi, free naps, rocking chairs, and frisbee golf

Graham Farm Cabin

Enjoy the country life in rural Greene Co in our cabin located on our farm. A great getaway spot! Features 2 bedrooms, 2 bathrooms, kitchen, dining, living room, laundry, porch and fire pit. Look out over the field for a beautiful sunrise. On a clear night, the stars are amazing! Enjoy nature and take a walk along our creek. Spend some time in our little town at our local shops and restaurants.... We live in the country between Carrollton and Jerseyville. (There is no WiFi.)

Riverfront Home in Calhoun County

Enjoy your relaxing experience nestled alongside the Illinois River in this private, riverfront property. You will be able to spend your time Eagle watching, fishing, or observing the barge traffic pass through the Joe Page Bridge. This space allows for the perfect country experience right on the back porch. The home is within walking distance of a public boat ramp and restaurant. For a short drive, you may find more restaurants, bars, grocery stores, and a gas station.

Hills and Hollers Lodge (Rental of Entire Lodge)

Hills and Hollers is an 8-Bedroom Lodge that was originally built to house whitetail deer and duck hunters. Surrounded by the Mississippi River and the Illinois River, Hills and Hollers Lodge is located in the heart of America's most beautiful farmland. Wildlife, orchards, fishing are all around Calhoun County and you'll be smack-dab in the middle of it. Mary and Marty are great hosts that will make you feel welcome and "at home" with a country feel at a budget price.

Pere Ridge Tree Escape

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a 10 minute drive to Grafton.