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

Holiday Rentals in Hillsboro

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (32 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 €193
includes taxes & fees
4 Nov - 5 Nov
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, (16 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 €222
includes taxes & fees
30 Nov - 1 Dec
Colorful getaway in friendly Driftless village

3. 6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (27 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 €617
includes taxes & fees
4 Nov - 5 Nov
6 Bedroom Home in Gods Country

4. 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, (36 reviews)
"Great location for our family outing. Plenty of room for everyone and a nice deck for relaxing outside. Easy ride to the Kickapoo River as well as surrounding towns for a little bumming."
United States
Dawn C.
The price is €714
includes taxes & fees
4 Nov - 5 Nov
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

5. 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, (90 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is €276
includes taxes & fees
4 Nov - 5 Nov
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

6. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (50 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 €138
includes taxes & fees
17 Nov - 18 Nov
Blakley Hobbit Large Cabin

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 €256
includes taxes & fees
17 Nov - 18 Nov
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC

8. 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, (21 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 €257
includes taxes & fees
17 Nov - 18 Nov
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

9. Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+

Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+
Camp Douglas
The price is €2,432
includes taxes & fees
4 Nov - 5 Nov
Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+

10. #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 €20
includes taxes & fees
17 Nov - 18 Nov
#10 Blakley Hobbit Campground-Tent spot

11. Soothing cabin 1 out of 7 in New Lisbon

Soothing cabin 1 out of 7 in New Lisbon
New Lisbon
9.2 out of 10, Wonderful, (7 reviews)
"Great location. Met our needs perfectly"
United States
Tricia C.
The price is €314
includes taxes & fees
4 Nov - 5 Nov
Soothing cabin 1 out of 7 in New Lisbon

12. 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 €104
includes taxes & fees
19 Nov - 20 Nov
Blakley Hobbit Small Cabin

13. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (35 reviews)
"A great place to get away and relax."
United States
Betsy D.
The price is €209
includes taxes & fees
1 Dec - 2 Dec
Your adventure begins the second you arrive!

14. 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 €342
includes taxes & fees
17 Nov - 18 Nov
The Incline

15. 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, (20 reviews)
"Good host and place was great for a brothers golf trip"
United States
Lee V.
The price is €437
includes taxes & fees
4 Nov - 5 Nov
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

16. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (64 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 €215
includes taxes & fees
17 Nov - 18 Nov
The Honey Haven

17. Amish Country Lodge | Peaceful Hot Tub Retreat

Amish Country Lodge | Peaceful Hot Tub Retreat
Hill Point
10.0 out of 10, Exceptional, (1 review)
"The property was lovely; clean, welcoming and spacious. Andrew was an attentive and helpful host."
United States
Maura M.
Amish Country Lodge | Peaceful Hot Tub Retreat

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 €357
includes taxes & fees
4 Nov - 5 Nov
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

19. Revilo Moose Ridge Mauston - Smoky Mt Vibes, Wisconsin Wild

Revilo Moose Ridge Mauston - Smoky Mt Vibes, Wisconsin Wild
Mauston
10.0 out of 10, Exceptional, (3 reviews)
"We celebrated my wife's 40th birthday there with friends.They had everything we needed and more. Paul was great and quick to respond.I would definitely stay there again!"
United States
Darius L.
Revilo Moose Ridge Mauston - Smoky Mt Vibes, Wisconsin Wild

20. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (54 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is €258
includes taxes & fees
16 Nov - 17 Nov
Cabin on the Kickapoo
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillsboro Hotel Reviews

Find out more about Hillsboro

Everything you need to know about Hillsboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsboro holiday rentals we have selected for you start as low as €138 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsboro rentals

At Expedia, we put the best Hillsboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.