Holiday houses in Hillsboro

Unique Apartment with Amazing Views

Abe’s Apartment is close to everything making it easy to plan your visit to downtown Vandalia. This loft offers a bedroom, full kitchen and bath, dining room, living room with a pull out sofa and large smart TV, and a remote work space. This loft also offers beautiful views of the oldest State Capitol in IL and is within walking distance to many restaurants, bars, and local shops. It is located on the 2nd level and will require you to climb 1 flight of stairs. For events please contact the host

Relaxing Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Cozy Tiny Home in Woods w/ Firepit & Porch Swing

Need a break? Some time to relax and breathe? Come get away from it all at this TINY HOME in the woods. Roast s'mores around the fire pit, go kayaking on nearby Carlyle Lake, stargaze on the porch swing with a cozy blanket...or just cuddle up and binge watch your favorite shows in front of the fireplace. Fully updated with everything you need: full size washer/dryer, stocked kitchen, smart TVs, wifi, outdoor grill, 2 RV hookups, space to park a boat - conveniently right off of I-70!

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

Cozy Home on College Ave

Welcome to our adorable two-bedroom home in the heart of Greenville! Nestled less than half a mile from Greenville University, this cozy retreat offers easy access to 1-70 and Greenville Square. Skip the traditional hotel and enjoy the comfort of a simple home at an affordable rate. With St. Louis just under an hour away, you'll experience the perfect blend of charm, convenience, and proximity to local attractions. Book now for a delightful stay in this inviting space!

ThE HiDeAwAy

You’ll be surprised by what’s inside! We’ve designed this space to be more than just a place to stay — it’s an experience, because isn’t that what life’s all about? Perfectly located just two blocks from the town square and only steps from the iconic Million Dollar Courthouse, you’ll also be close to great restaurants and shops. Whether you’re visiting for family, business, or a well-deserved getaway, we hope your stay with us creates lasting memories.

Relaxing House

Relax with the whole family at this peaceful new construction place to stay. Quiet neighborhood close to I-55 and historic Route 66. Beautiful, cozy new furnishings to make your stay very comfortable. Small town quaintness with community park close by with playground, fishing pond, quaint restaurants, and pickleball courts, as well as an area 9 hole public golf course just down the street. This space is a perfect to unwind and relax.

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

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.

House By The Woods 2 bedroom/sleeps 7

We have 2 electric fireplaces, 1 bathroom, 2 bedrooms, futon & full size bed in living room that sleeps up to 7 total. It has a side covered porch with a seating area & table with chairs. Firepit area for roasting hotdogs or marshmallows. Firewood on premises. Propane grill on back patio. Small kids play area in back yard & 4pm check in with 10am checkout.

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.