A red covered bridge in a forest.

Hillsboro Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Hillsboro holiday rentals

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

2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails
De Soto
The price is NZ$469
includes taxes & fees
27 Oct - 28 Oct
2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails

2. 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$418
includes taxes & fees
28 Sept - 29 Sept
Upstairs 2 bedroom Private Apt Off I- 55 in Pevely

3. 82 Acre Hobby Farm with Lincoln Log Cabin

82 Acre Hobby Farm with Lincoln Log Cabin
De Soto
10.0 out of 10, Exceptional, (47 reviews)
"This place was wonderful! We enjoyed our time staying here!"
United States
DeAnn H.
The price is NZ$482
includes taxes & fees
1 Oct - 2 Oct
82 Acre Hobby Farm with Lincoln Log Cabin

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$438
includes taxes & fees
28 Sept - 29 Sept
Cozy Serene home off 55 Queen Bed Smart TVs Wi-Fi

5. 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$447
includes taxes & fees
28 Sept - 29 Sept
Tiny Houses of French Village

6. 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$459
includes taxes & fees
28 Sept - 29 Sept
Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

7. Adorable small house - quiet & safe - 2 BR 1 Bath

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.0 out of 10, Wonderful, (14 reviews)
"Great place for a short get away"
United States
andytrower U.
Adorable small house - quiet & safe - 2 BR 1 Bath

8. Cozy Studio in the Heart of Downtown Kimmswick

Cozy Studio in the Heart of Downtown Kimmswick
Imperial
10.0 out of 10, Exceptional, (6 reviews)
"This was perfect for us! "
United States
Rebecca G.
The price is NZ$572
includes taxes & fees
28 Sept - 29 Sept
Cozy Studio in the Heart of Downtown Kimmswick

9. Cozy Studio in the Heart of Downtown Kimmswick

Cozy Studio in the Heart of Downtown Kimmswick
2.0 star property
Imperial
The price is NZ$466
includes taxes & fees
11 Oct - 12 Oct
Cozy Studio in the Heart of Downtown Kimmswick

10. Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 1-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$166
includes taxes & fees
30 Sept - 1 Oct
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

11. Clifford's Country Cottage

Clifford's Country Cottage
Bonne Terre
10.0 out of 10, Exceptional, (44 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$269
includes taxes & fees
28 Sept - 29 Sept
Clifford's Country Cottage

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

Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.
Byrnes Mill
10.0 out of 10, Exceptional, (23 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$533
includes taxes & fees
5 Oct - 6 Oct
Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.

13. Vive mol

Vive mol
3.0 star property
BONNE TERRE
The price is NZ$278
includes taxes & fees
28 Sept - 29 Sept
Vive mol

14. 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.
The price is NZ$1,142
includes taxes & fees
28 Sept - 29 Sept
Hot Tub + Fire Pit | Private Country Escape

15. Spacious Franklin County Retreat on 80 Acres!

Spacious Franklin County Retreat on 80 Acres!
3.0 star property
Luebbering
The price is NZ$1,910
includes taxes & fees
28 Sept - 29 Sept
Spacious Franklin County Retreat on 80 Acres!

16. 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, (74 reviews)
"I was a very nice place to stay. Very close to everything you need."
United States
Tina S.
The price is NZ$519
includes taxes & fees
28 Sept - 29 Sept
Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

17. Spacious Franklin County Retreat on 80 Acres!

Spacious Franklin County Retreat on 80 Acres!
Luebbering
9.8 out of 10, Exceptional, (9 reviews)
"Very spacious nice property. Family had a great time."
United States
kenneth
Spacious Franklin County Retreat on 80 Acres!

18. Beautiful historical two story stone farmhouse

Beautiful historical two story stone farmhouse
Bonne Terre
10.0 out of 10, Exceptional, (55 reviews)
"Great place to get away in a quiet country area. Definitely recommend it and would go back."
Canada
Jeannine
The price is NZ$756
includes taxes & fees
29 Sept - 30 Sept
Beautiful historical two story stone farmhouse

19. Downtown Kimmswick Studio Renovated Prime Location

Downtown Kimmswick Studio Renovated Prime Location
2.0 star property
Imperial
The price is NZ$510
includes taxes & fees
30 Sept - 1 Oct
Downtown Kimmswick Studio Renovated Prime Location

20. Kid and pet friendly 2 nd floor duplex

Kid and pet friendly 2 nd floor duplex
Pacific
9.0 out of 10, Wonderful, (30 reviews)
"The house was clean and comfortable. Would stay there again."
United States
Jason T.
The price is NZ$349
includes taxes & fees
28 Sept - 29 Sept
Kid and pet friendly 2 nd floor duplex
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.
Save an average of 15% on thousands of hotels when you're signed in

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 Lindwell 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.