Holiday houses in Hillsboro

The State Street Loft | Small Town Charm

Welcome to your spacious 1,700 SF 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.

Family · Value · Long stay

Cozy Chicken Cottage

Escape to your own peaceful oasis, where comfort meets tranquility, just steps away from a charming, rustic chicken coop. Immerse yourself in the serene sounds of nature on our tiny farm while you enjoy the fresh air. Start your day with a cup of coffee out on the front porch while you overlook our beautiful pond. Perfect for nature lovers, this peaceful hideaway invites you to unwind, recharge and connect with the rhythms of the country. 35 mins to downtown STL. 15 mins to Edwardsville.

Value · Location · Getting around

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!

Location · Family · Checkout

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!

Family · Location · Bathroom

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

Value · Family · Cleanliness

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.

Value · Family · Kitchen

Lake House off Route 66

Lake House Cabin is the best property in the area and offers a 2 acre lot at the end of a peninsula off Route 66. *Includes private lake access with fishing dock. *House has a fenced in dog area with doggie door. *Swimming, paddle boat and fishing allowed* *Crappie, bass bluegill, blue cat and channel cat. *Smoking allowed outside* *Pets 2 max *Crate pets when left alone. *4 person paddle boat *4 Guests Max including kids. *Wifi *No parties*

Value · Location · Parking

Relaxing 2 Bedroom 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.

Location · Value · Parking

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

Value · Location · Amenities

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!

Value · Family · View

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.

Value · Location · Walkability

Whitledge-Canaday House

This historical house is perfect for those who are deemed history buffs. This location brings back the old memories of the Canaday family while highlighting the little town of Hillsboro. This house embraces its past while incorporating a modern twist. Perfect for guests that are passing through, visiting family around the area, or those who simply want to relax.

Value · Family · Kitchen