Vacation rentals in Montgomery County

Historic Blackman-Evans Home

Centrally located on Main Street close to downtown Hillsboro. Step back in time where past meets present when you visit this historic home. You are surrounded by period furniture, while enjoying modern amenities such as A/C, WiFi, TVs, and luxury bedding. Built in the southern style, this creole-inspired cottage with a local stone foundation and original black walnut floors, stair case and wood work transports you to another time. Not suitable for small children, workgroups or pets. NO PETS.

Down on the Farm

Remote area that's about 15 min from Interstate 70. Quiet & peaceful w/minimal road traffic. Farming area. In warm weather, fish in our pond or visit/fish nearby Ramsey Lake State Park. Amish in the area & a local Amish market. Go for walks in our wooded area. Relax on a private deck in the evening. Queen bed, full bed, as well as a couch w/matching loveseat. NOTE on pets: 1 small pet under 25 lbs. allowed: PLEASE read our pet rules & agree to follow them before requesting a reservation.

Charming Hillsboro Home < 1 Mi to Downtown!

Experience the simple pleasures of small-town life from the comfort of 'The Cottage at 119,' a charming vacation rental in Hillsboro! Featuring a fully equipped kitchen, an inviting living room, and a convenient location near downtown, this renovated 1-bedroom, 1-bathroom getaway is the perfect place to call home. Stop by a local brewery, go fishing at Hillsboro Lake, or hike the trails at the H & B Bremer Wildlife Sanctuary! When you’re not exploring the area, relax in the lovely sunroom.

Rt 66 House; PETS WELCOME; FENCED YARD

Find all of our Litchfield homes by searching "softstays" on the internet. The Rt 66 house is on Historic Rt 66. It is 50 miles North of St. Louis; Right off I-55: PET FRIENDLY; FENCED BACK YARD. There is plenty of room to park a large U-Haul trailer. It is loaded with warm and updated furnishings. It has LOTS of 5* reviews. It has a thick memory foam queen bed. It has a coffee bar. You will hear trains. Two tracks run thru middle of town. 100 meg internet.

Lakehouse Two Bedroom Unit - The Historic Red Rooster Inn

The building has been renovated and two very special overnight accommodations have been created. The location is close to 4th of July Point, Sherwood Forest Campground, Glenn Shoals Lake South Marina, Hillsboro Country Club Golf Course, and is just a few miles from downtown Hillsboro. The tranquil lake setting will prove to be a peaceful retreat from hectic life and a wonderful place to unwind while visiting local family and friends

Private Getaway House w/ Pond & Trails on 10 Acres

Our place includes a recently remodeled home on 10 Acres in the middle of a country setting. There is a large patio area overlooking a half acre pond (fishing is catch and release only) right out of the front door. The property includes cleared trails to explore on, large grassy areas, a gravel driveway with ample parking, and a propane BBQ and deck out the kitchen door. Also has a ramp on the backside for wheelchair accessibility.

Downtown Hillsboro Loft

Two bedroom loft space in downtown Hillsboro located above a book and game store and next to a coffee shop and candy store! It’s also walking distance from a brewery, movie theater, live theater, ice cream shop and several local retail stores. The living space displays works of local artisans to complement the hint of mid-century style. With 1200 ft. of living space you will have room for everyone!

The Lake House

Quaint, cozy, cottage nestled on Beautiful Lake Vandalia. 1870’s farm house with all original decor. Full size granite bar located in 4 seasons room overlooking lake. Full size commercial kitchen. Stand up walk in shower, washer and dryer. Plenty of free safe parking. Perfect for a night stay or a full week vacation with family.

Willow's New House

Kick back and relax in this calm, stylish space. Located in a quaint, quiet community within walking distance to a golf course and ice cream. This new construction is easy to get to and not far from Historic Route 66 or I-55. Whether you're visiting family, or on your way through, Willow's house will feel just like your home!