A hidden ravine with a small shallow stream flowing between rock walls in Devil's Lake State Park near Baraboo, Wisconsin, USA.

Hillsboro Vacation Rentals

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Our top choices for Hillsboro vacation rentals

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, (27 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.
The price is CA $177
CA $296 total
includes taxes & fees
Jun 24 - Jun 25
Hillsboro Driftless Guesthouse is cozy and ready for you!

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, (2 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is CA $191
CA $270 total
includes taxes & fees
Jun 25 - Jun 26
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (43 reviews)
"Very peaceful, charming rustic cabin. I highly recommend and we plan to come back. "
United States
Jonathan C.
The price is CA $127
CA $239 total
includes taxes & fees
Jul 7 - Jul 8
Blakley Hobbit Large Cabin

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (29 reviews)
"Very secluded. Perfect for a weekend away. "
United States
Mathew D.
The price is CA $258
CA $308 total
includes taxes & fees
Jun 24 - Jun 25
Your adventure begins the second you arrive!

Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.8 out of 10, Good, (55 reviews)
"Enjoy our stay."
United States
Sondra M.
The price is CA $92
CA $172 total
includes taxes & fees
Jul 4 - Jul 5
Blakley Hobbit Small Cabin

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, (58 reviews)
"Nice place to stay right in town perfect for a couple "
United States
Pete G.
The price is CA $157
CA $279 total
includes taxes & fees
Jun 24 - Jun 25
Cozy first floor at the heart of downtown Viroqua

Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.8 out of 10, Exceptional, (46 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is CA $223
CA $452 total
includes taxes & fees
Jul 20 - Jul 21
Cabin on the Kickapoo

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (50 reviews)
"Excellent stay. Clean with beautiful surroundings and a great dog to greet you."
United States
Jason B.
The price is CA $226
CA $357 total
includes taxes & fees
Jun 25 - Jun 26
The Honey Haven

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 $71
CA $105 total
includes taxes & fees
Jun 24 - Jun 25
Blakley Hobbit Campground-RV spot #4

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, (1 review)
"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 CA $218
CA $516 total
includes taxes & fees
Jun 25 - Jun 26
Soothing cabin 1 out of 7 in New Lisbon

Rustic Tiny Haven in the Woods

Rustic Tiny Haven in the Woods
Lyndon Station
Rustic Tiny Haven in the Woods

The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (5 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
The price is CA $425
CA $511 total
includes taxes & fees
Jun 24 - Jun 25
The Incline

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.
The price is CA $119
CA $421 total
includes taxes & fees
Jun 24 - Jun 25
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC

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, (14 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is CA $255
CA $442 total
includes taxes & fees
Jun 25 - Jun 26
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

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.
The price is CA $329
CA $394 total
includes taxes & fees
Jul 19 - Jul 20
KwikStay: The Small-Town Ranch Style Home

Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub

Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub
Loganville
Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub

Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (14 reviews)
"It’s a cozy place with all cooking utensils you will ever need! Very comfy beds as well. "
United States
Randy R.
The price is CA $283
CA $372 total
includes taxes & fees
Jun 29 - Jun 30
Colorful getaway in friendly Driftless village

Secluded Rustic Cabin

Secluded Rustic Cabin
Cashton
9.8 out of 10, Exceptional, (55 reviews)
"What a wonderful property! "
United States
Becky K.
The price is CA $414
CA $688 total
includes taxes & fees
Jun 28 - Jun 29
Secluded Rustic Cabin

Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
Reedsburg
9.6 out of 10, Exceptional, (4 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 $318
CA $723 total
includes taxes & fees
Jun 24 - Jun 25
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

Scenic views on 20 acres! The Family Cabin awaits. Sleeps 10

Scenic views on 20 acres! The Family Cabin awaits. Sleeps 10
Elroy
9.8 out of 10, Exceptional, (8 reviews)
"Highly recommend to those that are looking for a relaxing getaway with a short commute to the Dells. "
United States
Cody
Scenic views on 20 acres! The Family Cabin awaits. Sleeps 10
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

Find out more about Hillsboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

This big old charming house Viroqua: This vacation home near Hillsboro offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.