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, (26 reviews)
"This house is very spacious and extra clean. The bed are comfortable and cozy. The house exceeded our expectations and we will definitely be staying here again."
United States
Shari S.
The price is CA $172
CA $271 total
includes taxes & fees
Mar 25 - Mar 26
Hillsboro Driftless Guesthouse is cozy and ready for you!

Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center

Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center
Richland Center
10.0 out of 10, Exceptional, (42 reviews)
"The hunters really enjoyed their stay. "
United States
Rhoda H.
The price is CA $206
CA $246 total
includes taxes & fees
Mar 25 - Mar 26
Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center

Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (45 reviews)
"Lovely little log cabin surrounded by trees. Hot tub was wonderful on a chilly night."
United States
Tanya W.
The price is CA $246
CA $474 total
includes taxes & fees
Mar 29 - Mar 30
Cabin on the Kickapoo

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
The price is CA $333
CA $401 total
includes taxes & fees
Mar 25 - Mar 26
Your adventure begins the second you arrive!

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, (67 reviews)
"Clean, pet friendly, great location"
United States
Matthew K.
The price is CA $124
CA $371 total
includes taxes & fees
Mar 25 - Mar 26
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Place of Peace - the Artist's Refuge

Place of Peace - the Artist's Refuge
La Farge
9.8 out of 10, Exceptional, (17 reviews)
"Easy in and out, the house had everything we needed, and the view was amazing!"
United States
shoua x.
The price is CA $179
CA $340 total
includes taxes & fees
Mar 28 - Mar 29
Place of Peace - the Artist's Refuge

Rustic Tiny Haven in the Woods

Rustic Tiny Haven in the Woods
Lyndon Station
The price is CA $91
CA $197 total
includes taxes & fees
Apr 1 - Apr 2
Rustic Tiny Haven in the Woods

Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (40 reviews)
"We enjoyed our stay, spending most of our time kayaking and hiking!! Beautiful quiet area and clean accommodations."
United States
Denise R.
The price is CA $124
CA $232 total
includes taxes & fees
Apr 2 - Apr 3
Blakley Hobbit Large Cabin

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 $291
CA $351 total
includes taxes & fees
Mar 25 - Mar 26
KwikStay: The Small-Town Ranch Style Home

Cozy 1-bedroom apartment with Private Hot-tub & Pool table

Cozy 1-bedroom apartment with Private Hot-tub & Pool table
Loganville
The price is CA $154
CA $192 total
includes taxes & fees
Apr 21 - Apr 22
Cozy 1-bedroom apartment with Private Hot-tub & Pool table

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (47 reviews)
"Quiet, clean, nestled in nature!"
United States
jim g.
The price is CA $220
CA $347 total
includes taxes & fees
Mar 30 - Mar 31
The Honey Haven

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, (54 reviews)
"Wonderful place! Clean, full of amenities, within walking distance to everything downtown has to offer."
United States
Alina L.
The price is CA $130
CA $245 total
includes taxes & fees
Mar 30 - Mar 31
Cozy first floor at the heart of downtown Viroqua

Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (12 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 $163
CA $230 total
includes taxes & fees
Mar 29 - Mar 30
Colorful getaway in friendly Driftless village

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
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is CA $247
CA $430 total
includes taxes & fees
Mar 30 - Mar 31
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Charming 2-bedroom Home in Reedsburg - 20min from Wisconsin Dells

Charming 2-bedroom Home in Reedsburg - 20min from Wisconsin Dells
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 $115
CA $406 total
includes taxes & fees
Apr 13 - Apr 14
Charming 2-bedroom Home in Reedsburg - 20min from Wisconsin Dells

Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
9.0 out of 10, Wonderful, (2 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is CA $69
CA $101 total
includes taxes & fees
Mar 25 - Mar 26
Blakley Hobbit Campground-RV spot #1

Wagonwheel Ranch

Wagonwheel Ranch
Viroqua
9.8 out of 10, Exceptional, (18 reviews)
"Quiet location nice setting. Great host "
United States
Josh K.
The price is CA $383
CA $707 total
includes taxes & fees
Mar 25 - Mar 26
Wagonwheel Ranch

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 $211
CA $501 total
includes taxes & fees
Mar 25 - Mar 26
Soothing cabin 1 out of 7 in New Lisbon

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Cashton
9.0 out of 10, Wonderful, (2 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.
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
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?

Lakeside cabin with Hot Tub and full kitchen! Sleeps up to 12 people.: This vacation home rental near Hillsboro is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.