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

Hillsboro Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Hillsboro holiday rentals

A living room with a television, a coffee table, a sofa, and a dining area in the background.

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)
"Nice place just outside city limits. Good spot to check out the area."
United States
Dan G.
The price is HK$1,009
HK$1,686 total
includes taxes & fees
28 Sept - 29 Sept
Hillsboro Driftless Guesthouse is cozy and ready for you!
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

2. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (15 reviews)
"Sweet home! Loved all the bright colored decorations! We had a great stay here with our bikes and pups. The porch was lovely to watch a thunderstorm from as well!"
United States
Emily B.
The price is HK$1,569
HK$2,052 total
includes taxes & fees
27 Sept - 28 Sept
Colorful getaway in friendly Driftless village
A wooden cabin with a porch, deck, and outdoor seating area.

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 HK$980
HK$1,423 total
includes taxes & fees
25 Sept - 26 Sept
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Two white hammocks hanging on a wooden porch with a view of a garden.

4. 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, (84 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is HK$992
HK$2,379 total
includes taxes & fees
27 Sept - 28 Sept
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

5. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (47 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 HK$706
HK$1,324 total
includes taxes & fees
29 Sept - 30 Sept
Blakley Hobbit Large Cabin
A two-story house with a balcony, surrounded by a forest.

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

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
10.0 out of 10, Exceptional, (12 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is HK$1,363
HK$2,829 total
includes taxes & fees
29 Sept - 30 Sept
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
A living room with a stone fireplace, a sofa, a chair, a coffee table, and a rug.

7. 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, (17 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 HK$1,765
HK$4,021 total
includes taxes & fees
25 Sept - 26 Sept
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
A cozy cabin interior with wooden walls, a stone fireplace, a dining area, and a kitchen with a large island.

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, (4 reviews)
"We had a very enjoyable stay. The cabin has a very cozy feel and worked great for a place to sleep! It is also not far away from things to do like Wisconsin Dells and Castle Rock Lake."
United States
Marnix H.
The price is HK$1,207
HK$2,879 total
includes taxes & fees
28 Sept - 29 Sept
Soothing cabin 1 out of 7 in New Lisbon
A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

9. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (57 reviews)
"Place is simple and cheap, could use some upkeep on building, door sticks and the water spigot for the sink drips and being held with duct tape. No bathroom just a portapotty to use. And watch out for the mice. It's a beautiful location on the west fork of the kickapoo River with access to the River."
United States
Timothy
The price is HK$510
HK$952 total
includes taxes & fees
26 Sept - 27 Sept
Blakley Hobbit Small Cabin
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

10. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (62 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 HK$1,255
HK$1,986 total
includes taxes & fees
1 Oct - 2 Oct
The Honey Haven
Two dogs sitting on a grassy field with a pond and trees in the background.

11. Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
The price is HK$392
HK$579 total
includes taxes & fees
29 Sept - 30 Sept
Blakley Hobbit Campground-RV spot #4
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

12. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
The price is HK$1,482
HK$1,779 total
includes taxes & fees
28 Sept - 29 Sept
Your adventure begins the second you arrive!
A modern interior with a wooden ceiling, a grey sofa, a staircase, and a kitchen area.

13. The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (7 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
The price is HK$2,353
HK$2,822 total
includes taxes & fees
28 Sept - 29 Sept
The Incline
A wooden cabin surrounded by snow-covered trees.

14. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (52 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 HK$1,122
HK$2,367 total
includes taxes & fees
5 Oct - 6 Oct
Cabin on the Kickapoo
A covered deck with outdoor furniture, a small table, and a grill.

15. Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.6 out of 10, Exceptional, (33 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is HK$2,675
HK$5,586 total
includes taxes & fees
28 Sept - 29 Sept
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

16. 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
9.0 out of 10, Wonderful, (18 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 HK$1,412
HK$2,457 total
includes taxes & fees
28 Sept - 29 Sept
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A spacious kitchen with wooden cabinets, a central island with stools, a dining area with a round table and chairs, and a ceiling fan.

17. 6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (26 reviews)
"It’s the good house and all the bed rooms have attached bathroom. Suggest to the homeowner is that keeping the bath shower and moisturizer at each room"
United States
Rambabu
The price is HK$4,236
HK$5,577 total
includes taxes & fees
26 Sept - 27 Sept
6 Bedroom Home in Gods Country
A dining area with a wooden table, white chairs, and a chandelier.

18. Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Cashton
9.6 out of 10, Exceptional, (4 reviews)
"Was in town for a wedding, it was a comfortable place. The master bedroom bed was comfortable and everything was very clean."
United States
Catherine T.
The price is HK$1,560
HK$2,829 total
includes taxes & fees
28 Sept - 29 Sept
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
A grey door with a window above it, a keypad lock, and a doorbell.

19. Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
10.0 out of 10, Exceptional, (61 reviews)
"I had a great trip to Viroqua and staying definitely had a hand in that. The location makes for a perfect jumping off point for day trips in the area, has plenty of restaurants in walking distance, and shops within a short drive. Wish I would have stayed longer."
United States
Robert H.
The price is HK$745
HK$1,338 total
includes taxes & fees
27 Sept - 28 Sept
Cozy first floor at the heart of downtown Viroqua
A row of wooden Adirondack chairs facing a calm lake surrounded by trees.

20. Charming 2-bedroom Loft cabin in serene New Lisbon

Charming 2-bedroom Loft cabin in serene New Lisbon
New Lisbon
10.0 out of 10, Exceptional, (1 review)
"Súper limpio lindo y cómodo ideal para una estancia relajante"
United States
Erica D Silverio
The price is HK$1,673
HK$4,189 total
includes taxes & fees
25 Sept - 26 Sept
Charming 2-bedroom Loft cabin in serene New Lisbon
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

Holiday Inn Express & Suites Reedsburg - Dells Area by IHG

Holiday Inn Express & Suites Reedsburg - Dells Area by IHG

10/10 Excellent
"The staff was very helpful and accommodating. Not all amenities were accessible and they did compensate for this. We have stayed at this hotel many times and have not been disappointed"
kelli 1-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Reedsburg - Dells Area by IHG

Find out more about Hillsboro

Search for holiday rentals in Hillsboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsboro using one of the methods below:

  • View our selection of featured holiday rentals in Hillsboro
  • Use the map to find apartments and other holiday homes in the Hillsboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsboro while they last

Look no further and take a look at our great range of rental properties in Hillsboro!

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.