A red covered bridge in a forest.

Hillsboro Vacation Rentals

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Our top choices for Hillsboro vacation rentals

1. 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 CA $214
CA $405 total
includes taxes & fees
Oct 18 - Oct 19
82 Acre Hobby Farm with Lincoln Log Cabin

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

2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails
De Soto
The price is CA $184
CA $377 total
includes taxes & fees
Oct 13 - Oct 14
2BR/1BA Pet-Friendly Escape Near Wineries & Hiking Trails

3. 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 CA $298
CA $339 total
includes taxes & fees
Oct 18 - Oct 19
Upstairs 2 bedroom Private Apt Off I- 55 in Pevely

4. 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 CA $107
CA $166 total
includes taxes & fees
Oct 13 - Oct 14
Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

5. 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 CA $312
CA $355 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Serene home off 55 Queen Bed Smart TVs Wi-Fi

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 CA $328
CA $374 total
includes taxes & fees
Oct 13 - Oct 14
Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

7. Downtown Kimmswick Studio Renovated Prime Location

Downtown Kimmswick Studio Renovated Prime Location
2.0 star property
Imperial
The price is CA $174
CA $418 total
includes taxes & fees
Oct 13 - Oct 14
Downtown Kimmswick Studio Renovated Prime Location

8. Downtown Kimmswick Studio~Renovated~Prime Location

Downtown Kimmswick Studio~Renovated~Prime Location
Imperial
9.0 out of 10, Wonderful, (2 reviews)
"We loved our stay! The location is convenient to so many great shops and other businesses. Walking everywhere we wanted to go was quick and easy. Everything in the rental looked new and spotless."
United States
Bette M.
The price is CA $227
CA $515 total
includes taxes & fees
Oct 13 - Oct 14
Downtown Kimmswick Studio~Renovated~Prime Location

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

Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.
Byrnes Mill
10.0 out of 10, Exceptional, (24 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 CA $214
CA $441 total
includes taxes & fees
Oct 21 - Oct 22
Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.

10. 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 CA $220
CA $487 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Studio in the Heart of Downtown Kimmswick

11. Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (77 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 CA $192
CA $316 total
includes taxes & fees
Oct 14 - Oct 15
Peter Ray House

12. 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 CA $282
CA $442 total
includes taxes & fees
Oct 13 - Oct 14
Tiny Houses of French Village

13. 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 CA $178
CA $219 total
includes taxes & fees
Oct 15 - Oct 16
Clifford's Country Cottage

14. Vive mol

Vive mol
3.0 star property
BONNE TERRE
The price is CA $123
CA $192 total
includes taxes & fees
Oct 13 - Oct 14
Vive mol

15. Spacious Franklin County Retreat on 80 Acres!

Spacious Franklin County Retreat on 80 Acres!
Luebbering
9.8 out of 10, Exceptional, (9 reviews)
"It was a lovely stay, too short."
United States
Reece
The price is CA $546
CA $1,563 total
includes taxes & fees
Oct 13 - Oct 14
Spacious Franklin County Retreat on 80 Acres!

16. Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (32 reviews)
"Lovely, quiet and comfortable place to stay. My son really enjoyed all the frogs and fresh air. "
United States
Kat O.
The price is CA $228
CA $405 total
includes taxes & fees
Oct 13 - Oct 14
Homestead Hideaway + Hot Tub

17. Cozy Studio in the Heart of Downtown Kimmswick

Cozy Studio in the Heart of Downtown Kimmswick
2.0 star property
Imperial
The price is CA $163
CA $387 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Studio in the Heart of Downtown Kimmswick

18. 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, (19 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 CA $257
CA $398 total
includes taxes & fees
Oct 15 - Oct 16
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

19. Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (49 reviews)
"Enjoyed our stay"
United States
Jason R.
The price is CA $205
CA $263 total
includes taxes & fees
Oct 13 - Oct 14
Pet and kid friendly duplex with 2 bedrooms

20. 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 CA $307
CA $509 total
includes taxes & fees
Oct 13 - Oct 14
Tiny Houses of French Village Tranquil & Relaxing
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Hillsboro?

Yes, we have vacation rentals close to top sights in Hillsboro, or you can select a secluded option if you're looking for a relaxing stay. Hillsboro is known for its parks and monuments.

What are some of the best vacation rentals in Hillsboro?

Charming 3-bedroom house in delightful Ballwin and basement is not included: This vacation home rental near 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 vacation rental in Hillsboro like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsboro. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a small group gathering.