Hillsboro Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Hillsboro vacation rentals

Fridge, microwave, oven, stovetop
Hillsboro Driftless Guesthouse is cozy and ready for you!

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)
"Stayed for a weeding at the brewery in town and this place was perfect. Had young kids that loved the big yard and park down the street. "
United States
Matt B.
$174 nightly
The price is $183
Dec 29 - Dec 30
Total with taxes and fees
Hillsboro Driftless Guesthouse is cozy and ready for you!
Dining
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!

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Lyndon Station
10.0 out of 10, Exceptional, (62)
"Clean, pet friendly, great location"
United States
Matthew K.
$248 nightly
The price is $262
Jan 26 - Jan 27, 2026
Total with taxes and fees
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Property grounds
Rustic Tiny Haven in the Woods

Rustic Tiny Haven in the Woods

Rustic Tiny Haven in the Woods
2.0 star property
Lyndon Station
$123 nightly
The price is $130
Jan 26 - Jan 27, 2026
Total with taxes and fees
Rustic Tiny Haven in the Woods
2 bedrooms, internet, bed sheets
Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center

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, (32)
"Overall awesome place "
United States
Brent m.
$172 nightly
The price is $181
Dec 28 - Dec 29
Total with taxes and fees
Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center
Exterior
Cabin on the Kickapoo

Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (44)
"Very cute! Had everything we needed! "
United States
jennie m.
$269 nightly
The price is $292
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cabin on the Kickapoo
Property grounds
Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
$70 nightly
The price is $74
Dec 28 - Dec 29
Total with taxes and fees
Blakley Hobbit Campground-RV spot #4
Microwave, oven, stovetop
Soothing cabin 1 out of 7 in New Lisbon

Soothing cabin 1 out of 7 in New Lisbon

Soothing cabin 1 out of 7 in New Lisbon
2.0 star property
New Lisbon
$348 nightly
The price is $367
Dec 30 - Dec 31
Total with taxes and fees
Soothing cabin 1 out of 7 in New Lisbon
Interior
The Honey Haven

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (46)
"Wonderful! Beautiful, serene place, clean environment, perfect!"
United States
Karen S.
$229 nightly
The price is $242
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Honey Haven
Fridge, microwave, oven, stovetop
Cozy first floor at the heart of downtown Viroqua

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, (52)
"Great convenience, quiet, well maintained, cute & cozy! Would definitely stay again! "
United States
Lynette W.
$160 nightly
The price is $178
Dec 28 - Dec 29
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
Fridge, microwave, coffee/tea maker, toaster
Quaint cabin overlooking the creek below and wetlands in the valley basin.

Quaint cabin overlooking the creek below and wetlands in the valley basin.

Quaint cabin overlooking the creek below and wetlands in the valley basin.
Norwalk
10.0 out of 10, Exceptional, (21)
"Beautiful cabin 100% recommend good communication "
Mexico
anayeli
$272 nightly
The price is $287
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quaint cabin overlooking the creek below and wetlands in the valley basin.
Terrace/patio
Place of Peace - the Artist's Refuge

Place of Peace - the Artist's Refuge

Place of Peace - the Artist's Refuge
La Farge
9.8 out of 10, Exceptional, (17)
"It was great! The place is calm and quiet and surrounded by beautiful nature. Best place to decompress before classes start."
United States
Claudia S.
$234 nightly
The price is $246
Dec 28 - Dec 29
Total with taxes and fees
Place of Peace - the Artist's Refuge
Exterior
Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (12)
"Beautiful house. We really enjoyed our stay. We highly recommend this location. "
United States
Eric M.
$223 nightly
The price is $235
Dec 28 - Dec 29
Total with taxes and fees
Colorful getaway in friendly Driftless village
Game room
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

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.6 out of 10, Exceptional, (8)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
$294 nightly
The price is $310
Dec 28 - Dec 29
Total with taxes and fees
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Fridge, microwave, oven, dishwasher
Hot-tub/King Bed/Snowmobile Trail @ The Hemlock

Hot-tub/King Bed/Snowmobile Trail @ The Hemlock

Hot-tub/King Bed/Snowmobile Trail @ The Hemlock
Loganville
10.0 out of 10, Exceptional, (6)
"Perfect spot for a group to stay. Four large bedrooms and large open concept kitchen living room make for lots of space. A short walk to quaint downtown restaurants. Highly recommended!"
United States
Lynn A.
$345 nightly
The price is $364
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hot-tub/King Bed/Snowmobile Trail @ The Hemlock
Interior
Ready to become a real love bird? Beautiful cabin to wake up hearing song birds

Ready to become a real love bird? Beautiful cabin to wake up hearing song birds

Ready to become a real love bird? Beautiful cabin to wake up hearing song birds
Norwalk
10.0 out of 10, Exceptional, (3)
"Easy check in. Beautiful cabin. We will be back for sure!"
United States
Dana S. S.
$322 nightly
The price is $340
Dec 28 - Dec 29
Total with taxes and fees
Ready to become a real love bird? Beautiful cabin to wake up hearing song birds
Property grounds
Blakley Hobbit Campground-Tent spot #9

Blakley Hobbit Campground-Tent spot #9

Blakley Hobbit Campground-Tent spot #9
Viola
10.0 out of 10, Exceptional, (1)
$40 nightly
The price is $42
Dec 28 - Dec 29
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #9
Property grounds
Blakley Hobbit Campground-Tent spot #10

Blakley Hobbit Campground-Tent spot #10

Blakley Hobbit Campground-Tent spot #10
Viola
10.0 out of 10, Exceptional, (3)
"The tent sites are right along the river. Not all of them have a fire pit, picnic table or grill but this is a lovely quiet serene spot to camp. "
United States
Deborah S.
$40 nightly
The price is $42
Dec 28 - Dec 29
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #10
Property grounds
Blakley Hobbit Campground-Tent spot #3

Blakley Hobbit Campground-Tent spot #3

Blakley Hobbit Campground-Tent spot #3
Viola
$40 nightly
The price is $42
Dec 28 - Dec 29
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #3
Property grounds
Blakley Hobbit Campground-Tent spot #4

Blakley Hobbit Campground-Tent spot #4

Blakley Hobbit Campground-Tent spot #4
Viola
10.0 out of 10, Exceptional, (2)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
$40 nightly
The price is $42
Dec 28 - Dec 29
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #4
Property grounds
6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (20)
"Super friendly and responsive owners. Went above and beyond to make sure our short stay was memorable. We biked during the day to Sparta and very easy access to the bike trail. Would highly recommend to anyone. "
United States
Susan K.
$623 nightly
The price is $657
Dec 28 - Dec 29
Total with taxes and fees
6 Bedroom Home in Gods Country
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
"We were totally impressed when pulling into the parking lot, loved the lodge look, then stepping into the lobby you could tell a lot of care and insight was put into the creation of this hotel. I was totally impressed with the cleanliness. The staff was all very friendly and caring. We will be back."
Peggy 1-night trip
Posted 5 days 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, 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 $181 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.

Explore a world of travel with Expedia

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?

Queen Anne Stay: This vacation home rental near Hillsboro has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.