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, (31 reviews)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
The price is NZ$385
includes taxes & fees
19 Oct - 20 Oct
Hillsboro Driftless Guesthouse is cozy and ready for you!

2. 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, (8 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is NZ$319
includes taxes & fees
14 Oct - 15 Oct
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

3. 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 NZ$464
includes taxes & fees
12 Oct - 13 Oct
Colorful getaway in friendly Driftless village

4. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (58 reviews)
"fishing cabin."
United States
joe
The price is NZ$216
includes taxes & fees
12 Oct - 13 Oct
Blakley Hobbit Small Cabin

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 NZ$301
includes taxes & fees
12 Oct - 13 Oct
Blakley Hobbit Large Cabin

6. 12 Mi to Castle Rock Lake: Serene New Lisbon Home!

12 Mi to Castle Rock Lake: Serene New Lisbon Home!
New Lisbon
10.0 out of 10, Exceptional, (4 reviews)
"Dated furnishing but clean, neat a n and well cared for. Handy location. Great hosts"
United States
nick k.
12 Mi to Castle Rock Lake: Serene New Lisbon Home!

7. 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
8.0 out of 10, Very good, (2 reviews)
"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$510
includes taxes & fees
1 Nov - 2 Nov
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC

8. 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, (87 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is NZ$554
includes taxes & fees
13 Oct - 14 Oct
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

9. #4 Blakley Hobbit Campground-Tent spot

#4 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
The price is NZ$75
includes taxes & fees
12 Oct - 13 Oct
#4 Blakley Hobbit Campground-Tent spot

10. 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, (5 reviews)
"Beautiful cozy cabin! Loved the gas fireplace! The cabin had everything we needed and we enjoyed our stay."
United States
Monica P.
The price is NZ$627
includes taxes & fees
12 Oct - 13 Oct
Soothing cabin 1 out of 7 in New Lisbon

11. 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 NZ$1,212
includes taxes & fees
12 Oct - 13 Oct
6 Bedroom Home in Gods Country

12. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"A great place to get away and relax."
United States
Betsy D.
The price is NZ$436
includes taxes & fees
14 Oct - 15 Oct
Your adventure begins the second you arrive!

13. 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 NZ$554
includes taxes & fees
12 Oct - 13 Oct
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

14. 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, (35 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is NZ$1,214
includes taxes & fees
13 Oct - 14 Oct
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

15. 12 Mi to Castle Rock Lake: Serene New Lisbon Home!

12 Mi to Castle Rock Lake: Serene New Lisbon Home!
3.0 star property
New Lisbon
12 Mi to Castle Rock Lake: Serene New Lisbon Home!

16. 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 NZ$132
includes taxes & fees
12 Oct - 13 Oct
Blakley Hobbit Campground-RV spot #4

17. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is NZ$75
includes taxes & fees
12 Oct - 13 Oct
#9 Blakley Hobbit Campground-Tent spot

18. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (53 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is NZ$546
includes taxes & fees
18 Oct - 19 Oct
Cabin on the Kickapoo

19. 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 NZ$436
includes taxes & fees
20 Oct - 21 Oct
The Honey Haven

20. Blakley Hobbit Campground-RV spot #3

Blakley Hobbit Campground-RV spot #3
Viola
6.0 out of 10, (1 review)
"This is a beautiful property. The price is a little high for the lack of amenities and the road was busier than I expected but we loved the place anyhow. "
United States
Kirstin
The price is NZ$132
includes taxes & fees
12 Oct - 13 Oct
Blakley Hobbit Campground-RV spot #3
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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?

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes: This holiday home rental outside of Hillsboro is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.