A red covered bridge in a forest.

Hillsboro Holiday Rentals

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Our top choices for Hillsboro holiday 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, (46 reviews)
"The cabin was wonderful with many extras like snacks and coffee."
United States
Janna B.
The price is NZ$480
includes taxes & fees
18 Aug - 19 Aug
82 Acre Hobby Farm with Lincoln Log Cabin

2. 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)
"The host was very responsive to all communication and our stay was very nice. It was a nice place to stay. It was comfortable and met are needs very well."
United States
Denise S.
The price is NZ$198
includes taxes & fees
19 Aug - 20 Aug
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

3. Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (75 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$376
includes taxes & fees
15 Aug - 16 Aug
Peter Ray House

4. 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, (11 reviews)
"We had a peaceful, quiet stay while visiting family in the area."
United States
Caren L.
The price is NZ$396
includes taxes & fees
20 Aug - 21 Aug
Upstairs 2 bedroom Private Apt Off I- 55 in Pevely

5. Clifford's Country Cottage

Clifford's Country Cottage
Bonne Terre
10.0 out of 10, Exceptional, (41 reviews)
"Great stay, very clean and comfortable."
United States
Chris G.
The price is NZ$259
includes taxes & fees
14 Aug - 15 Aug
Clifford's Country Cottage

6. Cozy Studio in the Heart of Downtown Kimmswick

Cozy Studio in the Heart of Downtown Kimmswick
Imperial
10.0 out of 10, Exceptional, (5 reviews)
"This was perfect for us! "
United States
Rebecca G.
The price is NZ$540
includes taxes & fees
16 Aug - 17 Aug
Cozy Studio in the Heart of Downtown Kimmswick

7. 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$422
includes taxes & fees
19 Aug - 20 Aug
Cozy Serene home off 55 Queen Bed Smart TVs Wi-Fi

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 NZ$584
includes taxes & fees
16 Aug - 17 Aug
Downtown Kimmswick Studio~Renovated~Prime Location

9. Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (6 reviews)
"I was a great experience loved everything about it"
United States
Alisha
The price is NZ$525
includes taxes & fees
17 Aug - 18 Aug
Tiny Houses of French Village

10. 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$336
includes taxes & fees
14 Aug - 15 Aug
Kid and pet friendly 2 nd floor duplex

11. Cozy Camper in Villa Ridge

Cozy Camper in Villa Ridge
Villa Ridge
9.2 out of 10, Wonderful, (5 reviews)
"Trailer was super clean and nice and exactly what I needed for the quick weekend. I enjoyed the stay."
United States
Carol M.
The price is NZ$206
includes taxes & fees
14 Aug - 15 Aug
Cozy Camper in Villa Ridge

12. 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$502
includes taxes & fees
26 Aug - 27 Aug
Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

13. Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (48 reviews)
"Enjoyed our stay"
United States
Jason R.
The price is NZ$314
includes taxes & fees
19 Aug - 20 Aug
Pet and kid friendly duplex with 2 bedrooms

14. 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, (16 reviews)
"Such a cute place to stay for a weekend getaway. Very clean and well stocked with things you may need. Loved being able to sit on the porch and watch the rain at night and reading next to the fire pit during the day. "
United States
Jennifer B.
The price is NZ$472
includes taxes & fees
16 Aug - 17 Aug
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

15. Salt & Honey Cottage Walk to Dining & Pet Friendly

Salt & Honey Cottage Walk to Dining & Pet Friendly
Waterloo
10.0 out of 10, Exceptional, (3 reviews)
"We loved staying here. It was the perfect location and and it was decorated beautifully. Would definitely stay here again. "
United States
Wendy B.
The price is NZ$458
includes taxes & fees
17 Aug - 18 Aug
Salt & Honey Cottage Walk to Dining & Pet Friendly

16. Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
Eureka
9.0 out of 10, Wonderful, (72 reviews)
"This was an extraordinary experience with great property and location and the description of the property was exact on. The host was very helpful when it came to anything we was needing very much appreciated and look forward to staying with this property owner again."
United States
Keith
The price is NZ$468
includes taxes & fees
26 Aug - 27 Aug
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

17. Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (31 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 NZ$472
includes taxes & fees
31 Aug - 1 Sept
Homestead Hideaway + Hot Tub

18. 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$593
includes taxes & fees
17 Aug - 18 Aug
Tiny Houses of French Village Tranquil & Relaxing

19. In the Country a Beautiful 2-bedroom house with its own private lake

In the Country a Beautiful 2-bedroom house with its own private lake
Waterloo
10.0 out of 10, Exceptional, (31 reviews)
"We loved everything about the property."
United States
Vince
The price is NZ$423
includes taxes & fees
19 Aug - 20 Aug
In the Country a Beautiful 2-bedroom house with its own private lake

20. 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
The price is NZ$1,854
includes taxes & fees
14 Aug - 15 Aug
Spacious Franklin County Retreat on 80 Acres!
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?

3-bedroom vacation home just 20 minutes from Six Flags St. Louis: This holiday home rental outside of Hillsboro is located on a river, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.