Vacation rentals in Montgomery County

Pheasant Valley Farms

Enjoy your stay in your very own farmhouse. Nestled in rolling hills, with views of the flowing creek and fields. Just 6 miles East of Hillsboro, IL & 45 minutes from Springfield, IL Enjoy hiking, fishing, golf, boating and relaxing on the porch. The farmhouse has 1 bedroom with a queen bed and comfortable sofa sleeper (double) in the living room. There is also a bed/futon in the summer kitchen (separate structure, no bathroom). Best used in cooler weather, no A/C. It is more of a man cave

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.

Loft Living | Small Town Charm

Welcome to your stylish home away from home in the heart of downtown Litchfield! This 2nd floor loft blends modern updates with old-town charm, featuring 3 comfy bedrooms, 1.5 bathrooms, and soaring ceilings that create an airy, open feel. Enjoy a space with plush seating, high-speed internet, and a workspace - perfect for both relaxation and work. Whether you're here for a weekend escape or an extended stay, this downtown loft is the perfect mix of comfort, style, and convenience.

Historic Stay in 1843 Blackman-Evans Home/Downtown

Listed on the National Register of Historic Places, this beautifully preserved home on Main Street near downtown Hillsboro features locally harvested, original, black walnut staircase, unique, original front door, and stone foundation quarried from the town of Alton Illinois. This historic home includes modern comforts including A/C, Wi-Fi, TVs and luxury bedding. To protect this historic property; no pets, no work crews, and passenger vehicles. No large trucks, trailers, or RVs.

Lakehouse Studio 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.

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!

Hillsboro Home

Centrally located in Hillsboro, our cozy 3-bedroom, 1-bath Airbnb offers comfort and convenience. Just minutes from downtown, restaurants, shops, laundromat, it's perfect for families or business travelers. Enjoy a fully equipped kitchen, fast Wi-Fi, and a relaxing stay in a quiet neighborhood.

2bedroom HOUSE close to downtown!

TWO bedroom family friendly house within walking distance of downtown Hillsboro! Kitchen, WIFI, washer & dryer, and full bathroom. Private driveway with additional parking space and a small backyard.

The Gathering Place

Your group will enjoy easy access to everything from The Gathering Place. Centrally located in downtown Nokomis, TGP doubles as a small event venue and an Air BNB that is both stylish and spacious!