Holiday houses 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

Spacious Lake home with fireplace & boatdock

Spacious cottage with spectacular views from all rooms of the home. Located on a 650 acre lake and hosts a 3.5 acre pond. Totally renovated with upscale kitchen and appliances. Large dining and entertaining area with a view of the lake and connecting sun room. Endless opportunities for variety of activities such as swimming, boating, kayaking, fishing, lawn games, hiking e,c. Home offers 2 bedrooms, 2 baths and a sleeper sofa. A gas fireplace enhances the living room with a desk for business

6-Acre Lake Estate: Boat Dock, Pool, Hot Tub, Pond

Escape to this spacious lakeside estate on 6 private acres! Perfect for groups, the open floor plan flows into an entertainment haven, complete with basement bar and shuffleboard. Outside, your private paradise awaits: dip in the pool, unwind in the hot tub, or fish the pond. Steps away, a private dock offers instant lake access. Nestled in a charming small town, this property blends secluded luxury with local convenience. Parking is a breeze with a spacious garage. Your lake retreat is here!

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.

The State Street Loft II | Downtown Retreat

Welcome to your spacious 1,700 SF home away from home in the heart of Downtown Litchfield! This beautifully renovated 2nd-floor loft features 3 bedrooms, 4 beds, and 2 full bathrooms. Enjoy brand-new furnishings throughout, including a luxurious Tempur-Pedic ProAdapt king mattress, high-speed Wi-Fi, and spacious living areas. Whether you're visiting for a weekend getaway, business trip, or Route 66 adventure, you'll love the perfect blend of comfort, style, and small-town charm.

Historic stay at the 1843 Blackman-Evans Home /4BR

Listed on the National Register of Historic Places, this beautifully preserved 1843 home is steps from downtown Hillsboro. Guests enjoy original architectural details including a locally harvested black walnut staircase, original front door, and stone foundation quarried from Alton, Illinois. Modern comforts include A/C, WiFi, smart TV's and luxury bedding. Experience he charm, history, and comfort of one of Illinois' treasured historic homes.

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 w/ Pond & Trails close to winery

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!

Edwards House; PETS WELCOME; FENCED YARD

PETS ARE WELCOME. Backyard is fenced. There's a tiled shower, a butcher block bar, king size memory foam bed. Rt 66 is close by. It has 100 meg wireless. There's NO CABLE TV and no local stations. The TV is a smart tv with apps. It is a perfect place to relax or “work from home”. There is digital door access. We'll give you the code, and wont bother you. There is a ring camera on the porch.

Willow's New 2 Bedroom 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!