Holiday rentals in Hillsboro

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.

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.

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*

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

Harrison House; PETS WELCOME; FENCED YARD

The Harrison House is a beautifully decorated 2-bedroom house that is in a safe neighborhood. WE ARE PET FRIENDLY. The beds are 12” queen memory foam. All the furnishings are new or nearly new. It has a fenced in backyard. KIDS ARE WELCOME. There is a back deck. There is no cable. There is 100 meg wireless internet. There is a ring camera on the porch. You will hear trains. Two tracks run thru middle of town

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 8th Hole

Enjoy a quiet country setting stay, on the edge of town. Only 2 miles from interstate 70. This is an upstairs luxury apartment with steep stairs to the entrance. It can accomodate up to 4 people comfortably. Vandalia has lots to offer. The historic Old State Capitol where Abraham Lincoln once visited , a walking trail in Rogier Park and beautiful Vandalia Lake.

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.

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!

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.

3 Bedroom, 2 bath cabin with deck and hot tub

Take it easy at this unique and tranquil getaway. Nestled across from Hillsboro Country Club Golf Course this location will have scenic views and be a great place to unwind and get away. Located near Sherwood Forest Campground, Glenn Shoals Lake, Hillsboro Lake as well as city parks.