Vacation rentals in Hillsboro

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Hillsboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Litchfield

5.0 out of 5 average rating, 6 reviews

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.

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Guest favorite

A welcoming living area features a light gray sofa with decorative pillows and a square glass coffee table. A modern accent chair is positioned beside the table, and a shelf displays simple décor. Natural light enters through a large window, creating a bright atmosphere.

Home in Greenville

4.96 out of 5 average rating, 244 reviews

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!

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Guest favorite

Home in Mount Olive

4.87 out of 5 average rating, 106 reviews

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*

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Superhost

A compact kitchenette is featured, showcasing black appliances including a refrigerator and stovetop oven. A sink with a modern faucet is set against a wooden countertop. Storage cabinets are present, and a clock is mounted on the wall. Natural light illuminates the space.

Apartment in Hillsboro

4.94 out of 5 average rating, 102 reviews

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

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Top guest favorite

A living area features a brown leather sofa and recliner, arranged around a wooden coffee table. A patterned area rug adds texture beneath the furniture. A colorful cow painting is displayed on the wall, while natural light filters through a nearby window.

Home in Litchfield

4.96 out of 5 average rating, 320 reviews

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

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Top guest favorite

A comfortable sofa is positioned in front of a vibrant accent wall featuring orange and blue geometric patterns. Natural light filters through a nearby window, illuminating the space, which is complemented by light wood flooring and neutral-colored walls.

Loft in Hillsboro

4.94 out of 5 average rating, 117 reviews

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!

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Top guest favorite

A single-story home is set on a well-maintained lawn, featuring a paved driveway leading to an attached garage. The exterior showcases a mix of light-colored siding and stone accents, framed by mature trees and shrubs, with large windows allowing natural light into the interior.

Home in Vandalia

5.0 out of 5 average rating, 177 reviews

Modern family friendly home in Historic Vandalia

Beautiful completely updated home with all new items. 2 blocks from the park and swimming pool, stroller in garage if needed. Across the road from the hospital, 2 blocks from public schools, 1 mile from walmart, close to many restaurants and coffee shop. Deck with outdoor seating and fenced in back yard and a corn hole game perfect for this beautiful back yard. And a charcoal grill ready to use.

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Top guest favorite

A spacious country home is shown, featuring a gray gravel driveway leading to the entrance. The structure has a sloped roof and a garage door. Vibrant yellow and red chairs are positioned outside, alongside potted plants and a sun shade, creating an inviting outdoor space.

Apartment in Vandalia

4.98 out of 5 average rating, 538 reviews

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.

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Guest favorite

The exterior of the historical home features a charming brick facade with a welcoming front porch. Colorful flowers are arranged along the walkway, and steps lead to the entrance. Large windows allow natural light to brighten the space, creating an inviting atmosphere.

Home in Hillsboro

4.91 out of 5 average rating, 53 reviews

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.

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Top guest favorite

Home in Raymond

4.98 out of 5 average rating, 43 reviews

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!

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Guest favorite

A single-story house is shown with a light-colored exterior. Steps lead to a covered porch, where a light fixture is visible beside the door. A gravel driveway and patches of green grass are present, surrounded by trees and a peaceful landscape.

Home in Hillsboro

4.94 out of 5 average rating, 36 reviews

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.

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Guest favorite

A well-equipped kitchen and dining area is highlighted by wooden cabinetry and a stone wall. A dining table with dark chairs sits across from modern appliances. A wood-burning stove is positioned beside large windows that invite natural light and views of the outdoor space.

Cabin in Hillsboro

4.94 out of 5 average rating, 290 reviews

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.

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