Hillsboro Holiday Rentals

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Holiday Rentals in Hillsboro

Property grounds
Driftless Area Country House: large deck, spring fed creek, Amish area
10.0 out of 10, Exceptional, (58)
"Very nice house with lots of room, good WiFi. Very dark at night with no moon, easy to sleep. I highly recommend this house!"
Driftless Area Country House: large deck, spring fed creek, Amish area
View from property
The Honey Haven
10.0 out of 10, Exceptional, (11)
"Had an excellent weekend get away! The Honey Haven is tucked away in an idyllic setting that is sure to recharge your soul. It is beautifully decorated, well thought out, and has a nice protective home energy. Add the charming local products, the sweetest welcoming dog, and the gorgeous stars above…and you can’t help but smile, breathe a sigh of relief while taking it all in. It is a much needed piece of heaven. Thank you!"
The price is NZ$412
per night
20 May - 21 May
The Honey Haven
Exterior
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
10.0 out of 10, Exceptional, (209)
"Outstanding! Great views, fire pit, right next to a great stream."
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
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Balcony
Secluded luxury cabin on 115 acres, 360 views, red cedar hot tub, Outdoor Shower
10.0 out of 10, Exceptional, (59)
"Had a wonderful time. Cabin was fully equipped and organized:) hot tub was amazing"
Secluded luxury cabin on 115 acres, 360 views, red cedar hot tub, Outdoor Shower
Fridge, microwave, oven, stovetop
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
10.0 out of 10, Exceptional, (215)
"Love this airy loft in Downtown Viroqua. Fishing buddies and I have stayed here twice, and will return next year! Owner is super-responsive and helpful. Fly shop is kitty-corner, Driftless Cafe is a block away. High-end grocery co-op is walking distance and delicious coffee shop on the same block."
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
Smart TV, fireplace
Cabin in Beautiful Timber Coulee
10.0 out of 10, Exceptional, (55)
"Convenient beautiful location. Enjoyed the surrounding communities."
Cabin in Beautiful Timber Coulee
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, (92)
"We enjoyed our stay at your lovely, beautifully decorated depot. The pictures online do not do it justice. The nature path nearby was ideal for morning walks. It was the perfect peaceful getaway."
Unique! A renovated old railroad depot turned into a cozy cottage.
Fridge, microwave, oven, stovetop
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (29)
"What a charming home! It was just as beautiful as the pictures, loved the view of the river, close to our daughter, loved cooking meals in the spacious kitchen & we loved ordering our food from The Port which was just up the road. The host (Holly) was very responsive and helpful. Hope to come back again!"
Relax with beautiful views overlooking the Wisconsin River
TV, fireplace, DVD player, books
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, (118)
"A beautiful cabin on a beautiful piece of land. As described in the listing and absolutely peaceful. This is our second time staying here and we will be back."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
Exterior
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
10.0 out of 10, Exceptional, (11)
"This is just what our souls needed. This beautiful home over exceeded any expectations. Quiet, peaceful, clean, and exquisite. It has everything you've ever wanted for a serene getaway. The owners are fabulous, and we are eternally grateful that they opened up this wonderful place to us. There is no doubt that we will be coming back and hopefully staying longer. Thank you so much!"
The price is NZ$490
per night
21 May - 22 May
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Fridge, microwave, oven, stovetop
Newly remodeled, private, sunny downtown apartment; near restaurants & shopping.
10.0 out of 10, Exceptional, (23)
"We enjoyed our time in the apartment. The apartment was nice, clean, and just the right size for the two of us. Guests should be aware that the apartment is upstairs and going up the stairs is required to access the apartment."
Newly remodeled, private, sunny downtown apartment; near restaurants & shopping.
Exterior
Tanager cabin at Driftless Creek
10.0 out of 10, Exceptional, (78)
"We had a wonderful time and will come back again! Modern cabin with great wifi and a lovely screened porch. Exactly what I was looking for."
Tanager cabin at Driftless Creek
Interior
Spacious Multi-family Log Home with Sauna
10.0 out of 10, Exceptional, (1)
"Could not have had a better birthday at this cabin! All 15 guests had sleeping arrangements and all comfortable. Ethan and his family were incredibly responsive and tended to our EVERY NEED! Very rural area, beautiful large cabin! Sauna was a lovely bonus! If you’re looking for a place to celebrate and relax- look no further! 5 stars- easily! Thank you for the opportunity to create memories with our big crew!"
Spacious Multi-family Log Home with Sauna
Exterior
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
10.0 out of 10, Exceptional, (5)
"Great place to enjoy the beautiful outdoors. Bluffs all around and trout streams everywhere. Loved it."
The price is NZ$351
per night
16 Jun - 17 Jun
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
Private kitchen
Cozy first floor at the heart of downtown Viroqua
9.8 out of 10, Exceptional, (20)
"It was a little hard to find. Just because we were arent front the area so the directions from the host helped immensely. The inside was extremely clean and cozy. The bed and couch were very comfortable and not stiff. Highly recommended, it definitely beats staying in the hotel."
The price is NZ$291
per night
20 May - 21 May
Cozy first floor at the heart of downtown Viroqua
Outdoor dining
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.8 out of 10, Exceptional, (59)
"Really cool property with amazing vintage details and antiques"
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Microwave, coffee/tea maker, cookware/dishes/utensils, dining tables
Willow Creek Cottage
9.8 out of 10, Exceptional, (61)
"2nd stay, and like the first time, everything was great. Hosts are super to deal with. Will definitely stay again when in the area."
Willow Creek Cottage
Exterior
Historic Bank Building on the Elroy-Sparta State Trail
9.8 out of 10, Exceptional, (42)
"We ran the marathon in Norwalk, from the entrance of the building to starting line was a 30 second walk. If you're going for the bike trail, thia ia the perfect place to stay."
The price is NZ$202
per night
21 May - 22 May
Historic Bank Building on the Elroy-Sparta State Trail
Exterior
Secluded Rustic Cabin
9.8 out of 10, Exceptional, (35)
"We enjoyed this cabin in spite of it’s fairly remote location. The deck, front porch, sunroom and fire pit gave it a homey and relaxing feel. The beds were very comfortable, and there were nicely renovated bathrooms. The property is a bird lovers’ paradise, with multiple feeders in the yard."
The price is NZ$587
per night
22 May - 23 May
Secluded Rustic Cabin
Property grounds
Private vacation house for larger groups near the Dells with heated game room.
9.6 out of 10, Exceptional, (40)
"Nice isolated place, a lot of amenities. Only negative is there is little to no cellphone connection. Kids loved the place so that was an extra plus!"
Private vacation house for larger groups near the Dells with heated game room.
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See all available properties in Hillsboro
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.

Other types of properties in Hillsboro you may be interested in

Lobby sitting area
The Lodge at Mauston
3.0 star property
9.6 out of 10, Exceptional, (312)
"Very clean and spacious room. The only negative was a loud furnace or AC unit (not sure which) that kicked on periodically and was extremely loud in the bedroom. "
The price is NZ$231
per night
22 May - 23 May
The Lodge at Mauston
Interior
AmericInn by Wyndham Mauston
2.0 star property
9.4 out of 10, Exceptional, (35)
"Quiet and clean. Needs updating "
The price is NZ$151
per night
29 May - 30 May
AmericInn by Wyndham Mauston
Standard Room, 1 Queen Bed with Sofa bed, Non Smoking, Jetted Tub (with Sofabed)
Best Western Park Oasis Inn
3.0 star property
9.0 out of 10, Wonderful, (564)
"Nice breakfast spread. Clean and quiet. "
The price is NZ$180
per night
19 May - 20 May
Best Western Park Oasis Inn
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.

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

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

Frequently asked questions

Can I find holiday rentals in Hillsboro?

Yes, there are holiday rentals close to the most popular sights in Hillsboro, or you can select a more secluded option if you're looking for a relaxing stay.

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 Wildcat Mountain State Park. In the wider area, you’ll find Lake Redstone and Kickapoo Valley Reserve Visitor Center.

What’s a holiday rental in Hillsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsboro. Holiday rentals feature extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip.

Recent reviews of Hillsboro properties
Expedia verified reviews