A red covered bridge in a forest.

Hillsboro Holiday Rentals

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Our top choices for Hillsboro holiday rentals

1. Upstairs 2 bedroom Private Apt Off I- 55 in Pevely

Upstairs 2 bedroom Private Apt Off I- 55 in Pevely
Pevely
9.6 out of 10, Exceptional, (12 reviews)
"We had a peaceful, quiet stay while visiting family in the area."
United States
Caren L.
The price is NZ$400
includes taxes & fees
15 Nov - 16 Nov
Upstairs 2 bedroom Private Apt Off I- 55 in Pevely

2. 82 Acre Hobby Farm with Lincoln Log Cabin

82 Acre Hobby Farm with Lincoln Log Cabin
De Soto
10.0 out of 10, Exceptional, (49 reviews)
"This place was wonderful! We enjoyed our time staying here!"
United States
DeAnn H.
The price is NZ$464
includes taxes & fees
15 Nov - 16 Nov
82 Acre Hobby Farm with Lincoln Log Cabin

3. 2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails

2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails
De Soto
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay! Has everything you need to entertain a Family. Lovely yard with lots of outdoor games. Clean and comfortable. The host was wonderful and communication was great. Will definitely be visiting again!"
United States
Stephen L.
The price is NZ$429
includes taxes & fees
8 Dec - 9 Dec
2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails

4. Cozy Serene home off 55 Queen Bed Smart TVs Wi-Fi

Cozy Serene home off 55 Queen Bed Smart TVs Wi-Fi
Pevely
9.8 out of 10, Exceptional, (8 reviews)
"Stay was nice quite and good location for us"
United States
James S.
The price is NZ$419
includes taxes & fees
15 Nov - 16 Nov
Cozy Serene home off 55 Queen Bed Smart TVs Wi-Fi

5. Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

Stay On Festus Main 2 bedroom 1.5 bath Near Mercy
Festus
10.0 out of 10, Exceptional, (1 review)
"Great property and location. Property was clean. Very convenient to local attractions. Communications with the host was fast and efficient. Will rent this property again in the future."
United States
Jennifer B.
The price is NZ$441
includes taxes & fees
16 Nov - 17 Nov
Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

6. Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Imperial
9.8 out of 10, Exceptional, (8 reviews)
"Thank you we enjoyed the place but we would like to get some more nights if all possible"
United States
Tommy H.
The price is NZ$177
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

7. Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.

Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.
Byrnes Mill
10.0 out of 10, Exceptional, (25 reviews)
"This was a repeat visit for us and we will always try to use this property - if available - when we come back to town! "
United States
Deborah W.
The price is NZ$534
includes taxes & fees
9 Dec - 10 Dec
Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.

8. Hot Tub + Fire Pit | Private Country Escape

Hot Tub + Fire Pit | Private Country Escape
Pacific
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful property, and well maintained home. Peaceful getaway. "
United States
Jon B.
Hot Tub + Fire Pit | Private Country Escape

9. Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (33 reviews)
"Spacious, comfortable, clean & quiet. And the dogs loved getting to roam around outside."
United States
Janice G.
The price is NZ$476
includes taxes & fees
15 Nov - 16 Nov
Homestead Hideaway + Hot Tub

10. Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (6 reviews)
"Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing "
United States
Chris
The price is NZ$607
includes taxes & fees
16 Nov - 17 Nov
Tiny Houses of French Village

11. Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (78 reviews)
"This house was incredible. Loved the history and ambience of the town. Peter was one of the nicest homes I’ve stayed in over the years. I would highly recommend it."
United States
Eric
The price is NZ$374
includes taxes & fees
15 Nov - 16 Nov
Peter Ray House

12. Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing
French Village
9.0 out of 10, Wonderful, (4 reviews)
"Great place to stay to get away from the rat race of busy life"
United States
Shannon S.
The price is NZ$587
includes taxes & fees
16 Nov - 17 Nov
Tiny Houses of French Village Tranquil & Relaxing

13. Beautiful historical two story stone farmhouse

Beautiful historical two story stone farmhouse
Bonne Terre
10.0 out of 10, Exceptional, (58 reviews)
"Great place to get away in a quiet country area. Definitely recommend it and would go back."
Canada
Jeannine
The price is NZ$721
includes taxes & fees
13 Nov - 14 Nov
Beautiful historical two story stone farmhouse

14. Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing
French Village
9.8 out of 10, Exceptional, (7 reviews)
"Everything is top notch at this property. Including the hospitality. Carisa goes out of her way to make sure you have everything you need. "
United States
James F.
The price is NZ$601
includes taxes & fees
25 Nov - 26 Nov
Tiny Houses of French Village Tranquil & Relaxing

15. Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!
Eureka
9.2 out of 10, Wonderful, (78 reviews)
"I thought the property was perfect for me and my buddies to enjoy a good weekend trip. This place is also very close to many fast foods and groceries stores, also six flags of course."
United States
Korbyn S.
The price is NZ$500
includes taxes & fees
13 Nov - 14 Nov
Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

16. Clifford's Country Cottage

Clifford's Country Cottage
Bonne Terre
10.0 out of 10, Exceptional, (48 reviews)
"This place is a gem! Country setting, but only a few minutes from shops and restaurants. New and extremely well stocked. Perfect for a couple looking to get away. Host is super responsive and accommodating! Will definitely be back."
United States
Philip
The price is NZ$260
includes taxes & fees
15 Nov - 16 Nov
Clifford's Country Cottage

17. Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Bloomsdale
10.0 out of 10, Exceptional, (20 reviews)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
United States
Blake H.
The price is NZ$481
includes taxes & fees
16 Nov - 17 Nov
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

18. Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (50 reviews)
"Unit was very clean and comfortable. Lots of space inside and outside for yard and parking. Host was responsive to our questions. Local restaurants with good food and service were nearby."
United States
John D.
The price is NZ$315
includes taxes & fees
29 Nov - 30 Nov
Pet and kid friendly duplex with 2 bedrooms

19. Kid and pet friendly 2 nd floor duplex

Kid and pet friendly 2 nd floor duplex
Pacific
8.8 out of 10, Excellent, (33 reviews)
"Very clean, nicely decorated."
United States
Amanda Q.
The price is NZ$328
includes taxes & fees
22 Nov - 23 Nov
Kid and pet friendly 2 nd floor duplex

20. Spacious, cozy home in Saint Louis

Spacious, cozy home in Saint Louis
St. Louis
10.0 out of 10, Exceptional, (47 reviews)
"Excellent communication and service, very clean, and nice place to stay. We enjoyed our stay!"
United States
Jennifer M.
The price is NZ$524
includes taxes & fees
23 Nov - 24 Nov
Spacious, cozy home in Saint Louis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsboro Hotel Reviews

Find out more about Hillsboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hillsboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hillsboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Hillsboro. Seeing all the best attractions is bound to make you fall in love with Hillsboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Hillsboro short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Hillsboro?

Yes, there are holiday rentals close to the most popular sights in Hillsboro, or you can select a more secluded option if you're looking for a relaxing stay. Hillsboro is known for its parks and monuments.

What are some of the best holiday rentals that Hillsboro has to offer?

Charming 3-bedroom house in delightful Ballwin and basement is not included: This holiday home rental outside of Hillsboro has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Hillsboro?

Big River and Cole Lake are a couple of lovely local spots to get outside and enjoy nature. Villa Antonio Winery and Sandy Creek Covered Bridge State Historic Site are other places to visit while you're in town.

What’s a holiday rental in Hillsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsboro. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a small group gathering.