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

Hillsboro Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Hillsboro vacation 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)
"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.
$205 nightly
The price is $216
Aug 31 - Sep 1
Total with taxes and fees
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.
$252 nightly
The price is $266
Aug 31 - Sep 1
Total with taxes and fees
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.
$172 nightly
The price is $181
Aug 30 - Aug 31
Total with taxes and fees
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

4. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (56 reviews)
"fishing cabin."
United States
joe
$115 nightly
The price is $121
Aug 30 - Aug 31
Total with taxes and fees
Blakley Hobbit Small Cabin
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, (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.
$160 nightly
The price is $169
Aug 30 - Aug 31
Total with taxes and fees
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
9.8 out of 10, Exceptional, (10 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
$313 nightly
The price is $330
Sep 22 - Sep 23
Total with taxes and fees
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Two white hammocks hanging on a wooden porch with a view of a garden.

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, (81 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
$295 nightly
The price is $311
Sep 28 - Sep 29
Total with taxes and fees
Charming cabin getaway in the woods, private trails, only 20 mins from WI 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, (3 reviews)
"Great location. Met our needs perfectly"
United States
Tricia C.
$348 nightly
The price is $367
Aug 30 - Aug 31
Total with taxes and fees
Soothing cabin 1 out of 7 in New Lisbon
A living room with a sofa, armchairs, a coffee table, and a lamp.

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.
$486 nightly
The price is $513
Aug 30 - Aug 31
Total with taxes and fees
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
A modern living room with a sectional sofa, a wooden coffee table, and a dining area with a white table and chairs.

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.
$265 nightly
The price is $295
Sep 8 - Sep 9
Total with taxes and fees
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
Two dogs sitting on a grassy field with a pond and trees in the background.

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.
$40 nightly
The price is $42
Aug 30 - Aug 31
Total with taxes and fees
#10 Blakley Hobbit Campground-Tent spot
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.
$196 nightly
The price is $207
Aug 31 - Sep 1
Total with taxes and fees
Your adventure begins the second you arrive!
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

13. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (59 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.
$240 nightly
The price is $253
Sep 2 - Sep 3
Total with taxes and fees
The Honey Haven
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

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.
$297 nightly
The price is $313
Aug 30 - Aug 31
Total with taxes and fees
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A modern kitchen with a white countertop, a black and white tiled backsplash, and a stainless steel oven.

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.
$352 nightly
The price is $371
Aug 31 - Sep 1
Total with taxes and fees
KwikStay: The Small-Town Ranch Style Home
A wooden cabin surrounded by snow-covered trees.

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.
$273 nightly
The price is $296
Sep 2 - Sep 3
Total with taxes and fees
Cabin on the Kickapoo
A grey door with a window above it, a keypad lock, and a doorbell.

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.
$160 nightly
The price is $178
Aug 31 - Sep 1
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
A wooden cabin with a porch and string lights, surrounded by trees.

18. 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.
$210 nightly
The price is $222
Sep 11 - Sep 12
Total with taxes and fees
Country Living at its Finest
A spacious living area with a fireplace, a sofa, a dining table, and a staircase leading to an upper level.

19. 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.
$343 nightly
The price is $362
Sep 8 - Sep 9
Total with taxes and fees
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

AmericInn by Wyndham Viroqua

AmericInn by Wyndham Viroqua

8/10 Good
"Handicap walkin shower was half the length of a tub. Easy to use. Bathroom was handicap friendly."
Keith 4-night trip
Posted 11 hours ago
AmericInn by Wyndham Viroqua

Find out more about Hillsboro

Everything you need to know about Hillsboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Hillsboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillsboro rentals

At Expedia, we put the best Hillsboro vacation 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 vacation.

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 vacation rentals in Hillsboro?

Yes, we have vacation rentals close to well known points of interest in Hillsboro, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Hillsboro has to offer?

Upper Place Vacation Cottage: This vacation home rental near Hillsboro is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the 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 larger area, you’ll find Wildcat Mountain State Park and Kickapoo Valley Reserve.

What’s a vacation rental in Hillsboro like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Hillsboro. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.