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Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A cozy cabin is situated among lush greenery, featuring a spacious deck that extends from the entrance. The gravel driveway leads up to the cabin, surrounded by trees and wild foliage, creating a serene, natural atmosphere.
Cabin in Westby
4.99 out of 5 average rating, 111 reviews

Nature’s Nest

Unwind and immerse yourself in nature at this cozy cabin overlooking Timber Coulee Creek. Large living room windows and a spacious deck provide you with a bird’s eye view of the rippling river and many types of wild life. Deer amble through the property; eagles soar and keep an eagle eye on everything. Turkeys, squirrels, coons, and myriad of birds go about their business in this serene environment. Trout fishing is an excellent pastime for those who care to cast a line. Rest, at Nature’s Nest.

Guest favorite
The exterior of the round yurt-style cabin is partially surrounded by lush greenery, with a wooden deck featuring a small seating area. A brick patio includes a built-in fire ring and a charcoal grill, creating a cozy outdoor space for gatherings.
Tiny home in Richland Center
4.91 out of 5 average rating, 278 reviews

Little Round Cabin on the Pine 2 - The "Pine Cone"

The 250 square foot "Pine Cone" is a one room, round yurt-style cabin located on our 8 acre property. We border the Pine River in Richland County, center of the beautiful Driftless region of southwest Wisconsin. Perfect for a quiet, nature-based retreat, we are less than four hours drive from Chicago, Milwaukee, and the Twin Cities. Staying with us supports our nonprofit, My Renewed Hope, which assists those living with or recovering from cancer. Read on for more info about the space and area.

Top guest favorite
A charming log cabin is situated atop a gentle hill, surrounded by lush greenery. The cabin features a spacious deck and is accessed by a set of wooden stairs. Bright blue skies and tall trees enhance the serene outdoor setting.
Cabin in Forest
4.97 out of 5 average rating, 173 reviews

Driftless Trout Cabin - Hillsboro, Wisconsin

Welcome to our spring-fed cordwood log cabin on 5.66 acres in Wisconsin’s beautiful Driftless region. Enjoy: - World class trout fishing for native brookies or abundant browns - Hiking nearby at the breathtaking Wildcat Mountain State Park or the 8,569 acre Kickapoo Valley Reserve - Canoeing or kayaking the beautiful Kickapoo River - Biking renowned bikes trails through the countryside - Sipping Wonderstate Coffee or Driftless Glen Bourbon on the deck while listening to the babbling spring

Top guest favorite
A modern living area features hardwood floors and large windows allowing natural light. An olive green sofa is flanked by light-colored chairs and a wooden side table. Decorative vintage posters adorn the walls, alongside a bookshelf filled with various items.
Apartment in Hillsboro
4.95 out of 5 average rating, 122 reviews

Yuba State Bank Apartment

The Yuba State Bank Apartment is the lower front apartment in a 4-unit commercial brick building. The historically renovated space has a mix of old and new, with hardwood floors, large storefront windows, a full kitchen and bathroom, and the bank vault off one of the two bedrooms. The apartment is located in the quaint village of Yuba (pop. 53), which is the smallest incorporated village in Wisconsin, 15 minutes (11 miles) from Hillsboro. You can grab a drink and meal next door at Louie's Bar.

Top guest favorite
A rustic cabin features wood siding and large windows, providing natural light. A welcoming porch with railings extends across the front, overlooking a grassy area. The surrounding landscape includes blooming trees and a hint of outdoor equipment nearby.
Farm stay in Ontario
4.94 out of 5 average rating, 271 reviews

Rustic cabin in an orchard at Echo Valley Farm

Rustic cabin near Wildcat Mountain State Park and Kickapoo Valley Reserve. A quiet place to disconnect, hike, and enjoy the Driftless. The cabin has electricity, supplied water and a non chemical port-o-let, a heater, wood stove (we supply all indoor wood), fire pit and charcoal grill. Our Bakery is open Saturday-Sunday 9-4, May -October or order in advance off season. Short walk from parking to the cabin; we will transport your gear if needed. Enjoy our trails! LGBTQ owned. BIPOC welcome.

Top guest favorite
Cabin in Adams
4.94 out of 5 average rating, 463 reviews

Cozy Log Cabin in the Woods

Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

Top guest favorite
The cottage is nestled among mature trees, featuring a welcoming white exterior with multiple windows. A spacious lawn surrounds the home, offering a peaceful view of the rolling hills in the background. The sky is partly cloudy, allowing natural light to illuminate the property.
Cottage in Ontario
4.99 out of 5 average rating, 131 reviews

Cozy stay at base of Wildcat Mt- Driftless Hygge!

Get cozy in the Driftless Hygge Cottage, right at the base of Wildcat Mountain State Park. The cottage is over 100 years old, but newly re-designed with your utmost coziness in mind. In the heart of the Driftless region of Wisconsin, stay in the remarkable beauty of the rolling hills, bluffs, and world-class trout streams. Just at the edge of the village city limits makes the amenities of the small village within walking distance, but still have privacy around a campfire taking in the views!

Guest favorite
Home in Richland Center
4.91 out of 5 average rating, 127 reviews

The Sweet Suite

The Sweet Suite is an upper duplex unit. We are located in the middle of the Driftless Area known for its scenic beauty and charm. A comfortable country atmosphere ideal for relaxation. We welcome traveling nurses! Feel free to inquire about a longer stay. The distance is: 8 miles to Richland Hospital in Richland Center 19 miles to Muscoda Health Center in Muscoda 24 miles to Gundersen St Joseph's Hospital in Hillsboro The location is also ideal for hunters and other sports enthusiasts.

Top guest favorite
An outdoor fire pit area is surrounded by blue adirondack chairs, set on a gravel circle. Lush green hills and trees form a scenic backdrop under a partly cloudy sky. Colorful flowers line the pathway leading from the house to the fire pit.
Home in Richland Center
5 out of 5 average rating, 116 reviews

Twin Pines Ridgetop Home

All new renovated home atop a beautiful bluff in the Driftless Area. This house is set perfect for some of the most beautiful views in the area. Enjoy a cup of coffee around the gas fire pit on the front porch overlooking the the valley. Then transition to the back porch at night for more great views around the campfire. Everything about this house and the area will make you want to stay longer. Come stay at Twin Pines! ●41 miles from Wisconsin Dells ●42 miles from Devils Lake State Park

Top guest favorite
A durable fabric shelter is set amidst lush greenery, featuring an inviting porch with outdoor seating. Flower boxes are trimmed with vibrant blooms, and a picnic table is positioned nearby. The structure is designed for comfort, blending seamlessly with the natural surroundings.
Campsite in Kendall
4.89 out of 5 average rating, 147 reviews

Driftless Bluff Glamping Cabin, Peaceful, Secluded

Rustic forest glamping in a heavy duty waterproof fabric shelter, 14 x 20ft. with a 5ft. awning. The perfect get away from it all, relax and enjoy nature. Flashlights, solar lights, propane 2-burner stove, and fire pit with grate. Kitchen set up with dishes, silverware, fully stocked coffee bar, filter water pitcher, shower bucket and most everything else. Compost toilet and foot pump sink. Small wood stove for when it's cold and a fan for when it's hot with battery to charge extras.

Guest favorite
A rustic cabin sits surrounded by autumn foliage, showcasing a covered porch with railings. The exterior features a wooden structure with a metal roof, blending harmoniously with the wooded landscape. A hammock is visible in the distance beneath the trees.
Cabin in La Farge
4.94 out of 5 average rating, 212 reviews

Back Roads Cabin Retreat

Enjoy a weekend off the grid in our rustic cabin on 30 acres of wooded serenity. Watch the sunset on the covered porch, or relax around a campfire. Feel free to explore the woods taking a hike on the network of trails. Nearby you can visit winery's, Wildcat Mountain State Park, the Kickapoo Valley Reserve and more. The driftless region is known for great fishing, scenic drives through the hills and biking. Contact us about additional camp sites on the property for larger groups.

Top guest favorite
A single-level home is surrounded by a well-maintained lawn, featuring green grass and a gravel road. The exterior showcases a combination of gray siding and a welcoming porch with seating, bordered by small plants and trees.
Home in Richland Center
4.95 out of 5 average rating, 277 reviews

Gramps Getaway

Gramps Getaway is a spacious 3 bedroom 2 Bath home five minutes from Richland Center, Featuring a new Amish made kitchen and lots of open spaces. Located on a quiet Lane, enjoy hiking, bicycling, or simply enjoy the quietness of country life. Gramps Getaway is a family friendly, all on one level home, You will enjoy the comfy gas fireplace in the Sun Room We have a gas grill on the back deck, lots of yard to roam and a life size Checker board and fire pit area for your enjoyment!

Popular amenities for Hillsboro vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Vernon County
  5. Hillsboro