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

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)
"Nice place just outside city limits. Good spot to check out the area."
United States
Dan G.
The price is CA $181
CA $299 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $281
CA $370 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $175
CA $252 total
includes taxes & fees
Sep 25 - Sep 26
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 CA $187
CA $435 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $126
CA $222 total
includes taxes & fees
Sep 24 - Sep 25
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, (11 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is CA $244
CA $503 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $316
CA $674 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $216
CA $512 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $91
CA $170 total
includes taxes & fees
Sep 26 - Sep 27
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, (61 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 CA $225
CA $355 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $70
CA $80 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $276
CA $330 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $421
CA $502 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $201
CA $423 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $479
CA $999 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $253
CA $440 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $758
CA $998 total
includes taxes & fees
Sep 26 - Sep 27
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 CA $279
CA $503 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $133
CA $235 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $299
CA $747 total
includes taxes & fees
Sep 24 - Sep 25
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

The Lodge at Mauston

The Lodge at Mauston

10/10 Excellent
"Pool, hot tub, and fitness room are all great. Breakfast was hot and fresh and had lots of options. Hotel was clean and well maintained, room was very spacious and nice."
Madeline 1-night trip
Posted 7 hours ago
The Lodge at Mauston

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsboro vacation rentals we have selected for you start as low as CA $170 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 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 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.