A forested river with clear water reflecting trees and rocky cliffs.

Hillsboro Holiday Rentals

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Our top choices for Hillsboro holiday rentals

1. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (29 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
The price is NZ$354
includes taxes & fees
2 Sept - 3 Sept
Hillsboro Driftless Guesthouse is cozy and ready for you!

2. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (15 reviews)
"It’s a cozy place with all cooking utensils you will ever need! Very comfy beds as well. "
United States
Randy R.
The price is NZ$432
includes taxes & fees
16 Sept - 17 Sept
Colorful getaway in friendly Driftless village

3. Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Ontario
10.0 out of 10, Exceptional, (6 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is NZ$300
includes taxes & fees
9 Sept - 10 Sept
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

4. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (56 reviews)
"fishing cabin."
United States
joe
The price is NZ$203
includes taxes & fees
3 Sept - 4 Sept
Blakley Hobbit Small Cabin

5. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (46 reviews)
"A quiet spot w excellent scenery along the Kickapoo River. Great communication w host & easy check-in/out process."
United States
Rebecca B.
The price is NZ$282
includes taxes & fees
31 Aug - 1 Sept
Blakley Hobbit Large Cabin

6. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
9.8 out of 10, Exceptional, (10 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is NZ$548
includes taxes & fees
22 Sept - 23 Sept
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

7. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Lyndon Station
10.0 out of 10, Exceptional, (80 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is NZ$549
includes taxes & fees
17 Sept - 18 Sept
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

8. Soothing cabin 1 out of 7 in New Lisbon

Soothing cabin 1 out of 7 in New Lisbon
New Lisbon
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Met our needs perfectly"
United States
Tricia C.
The price is NZ$607
includes taxes & fees
3 Sept - 4 Sept
Soothing cabin 1 out of 7 in New Lisbon

9. Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
Reedsburg
9.8 out of 10, Exceptional, (14 reviews)
"The home was very comfortable and clean. It had everything we needed and we would definitely stay here again! "
United States
Ken M.
The price is NZ$851
includes taxes & fees
28 Aug - 29 Aug
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

10. 2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC

2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
Reedsburg
10.0 out of 10, Exceptional, (1 review)
"I was in Reedsburg for work and this property was perfect. Had all the amenities that I needed and that were listed in the property details. I would definitely stay here again."
United States
Kerri M.
The price is NZ$484
includes taxes & fees
14 Sept - 15 Sept
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC

11. #10 Blakley Hobbit Campground-Tent spot

#10 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Huan B.
The price is NZ$71
includes taxes & fees
6 Sept - 7 Sept
#10 Blakley Hobbit Campground-Tent spot

12. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
The price is NZ$366
includes taxes & fees
31 Aug - 1 Sept
Your adventure begins the second you arrive!

13. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (58 reviews)
"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."
United States
Eric R.
The price is NZ$420
includes taxes & fees
2 Sept - 3 Sept
The Honey Haven

14. Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.2 out of 10, Wonderful, (17 reviews)
"excellent out of the way retreat close to things we wanted to do and great place for us and our cats, the hot tub was a great treat"
United States
Joseph W.
The price is NZ$508
includes taxes & fees
6 Sept - 7 Sept
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

15. KwikStay: The Small-Town Ranch Style Home

KwikStay: The Small-Town Ranch Style Home
Loganville
10.0 out of 10, Exceptional, (6 reviews)
"Home was absolutely beautiful with plenty of room for everyone. Centrally located to all attractions, with short travel times. Host was amazing to work with. "
United States
Dawn B.
The price is NZ$365
includes taxes & fees
31 Aug - 1 Sept
KwikStay: The Small-Town Ranch Style Home

16. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (48 reviews)
"Fun little place. Perfect for me and the wife. Close to Kickapoo area hiking. Hot tub was a nice touch to the neat little stay."
United States
Joel M.
The price is NZ$497
includes taxes & fees
2 Sept - 3 Sept
Cabin on the Kickapoo

17. Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
9.8 out of 10, Exceptional, (59 reviews)
"It was very clean. Perfectly located in quaint downtown Viroqua."
United States
Rose B.
The price is NZ$298
includes taxes & fees
30 Aug - 31 Aug
Cozy first floor at the heart of downtown Viroqua

18. Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub

Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub
Loganville
The price is NZ$313
includes taxes & fees
31 Aug - 1 Sept
Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub

19. Country Living at its Finest

Country Living at its Finest
Viroqua
9.8 out of 10, Exceptional, (238 reviews)
"Great cabin -private but close enough to town and near many trout streams."
United States
jennifer g.
The price is NZ$365
includes taxes & fees
11 Sept - 12 Sept
Country Living at its Finest

20. The Hilltop

The Hilltop
Norwalk
9.6 out of 10, Exceptional, (12 reviews)
"Clean, well supplied, had everything we needed. Basic cooking utensils were there, very comfortable, water was great, AC worked well, very cozy!"
United States
Anatole W.
The price is NZ$598
includes taxes & fees
27 Aug - 28 Aug
The Hilltop
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.

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

Upper Place Vacation Cottage: This holiday home rental outside of Hillsboro is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind.

What can I see and do in Hillsboro?

While exploring the area, visit family-friendly sights like The Red Geranium Framing and Gifts, or get outside and enjoy nature at Lake Redstone. In the wider area, you’ll find Wildcat Mountain State Park and Kickapoo Valley Reserve.

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 feature extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip.