Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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Top guest favorite

A spacious living area features a stone fireplace and large windows offering views of the surrounding landscape. Comfortable seating is arranged around a central coffee table, with a combination of wood and upholstered furniture contributing to a cozy atmosphere. Natural light brightens the room.

Home in La Farge

4.97 out of 5 average rating, 187 reviews

Kickapoo Lookout Retreat

Location, comfort, and views for miles! This sanctuary is minutes from the Kickapoo Valley Reserve, Wildcat Park and nestled on 10 private acres with stellar views from the wraparound deck. This is THE place to immerse in nature then relax with a meal and a cozy fire. Soak your tired muscles in the claw foot tub after a fun day out exploring. Enjoy the cold A/C or the efficient fireplace, chef's kitchen. Families enjoy the infant/kid gear, and clean single level space for a low stress retreat

Guest favorite

A rustic log cabin is framed by green trees, featuring a steeply pitched roof and decorative wood accents. A welcoming front porch leads to a door with a unique design, while a large window showcases flowing red curtains, blending natural elements with cabin charm.

Cabin in Ontario

4.93 out of 5 average rating, 114 reviews

Country Living Cabin

Brush Creek Log Cabins is your perfect get away for couples or the whole family. If you are looking to relax, do some recreational activities like canoeing , bike riding, hiking, antiquing and Amish shopping or spend time with that special someone you can find it just a few hours from home. We are in between Ontario and Cashton, off of Hwy 33. Over looking the Amish farms below. There are fairs and festivals many with tractor pulls nearby. Warrens cranberry festival and the Dells are nearby.

Top guest favorite

A modern kitchen and dining area are showcased, featuring wooden beams overhead and elegant cabinetry. A dining table is set for four, and stainless steel appliances are visible. Warm lighting casts a glow, creating a welcoming atmosphere in the space.

Bungalow in Richland Center

5 out of 5 average rating, 307 reviews

Glory View Ridgetop Bungalow

Farmhouse Bungalow sits on top of a ridge in the Southwest WI driftless area, boasting spectacular views. A site that works for anyone from a relaxing retreat to a great spot for adventures. Fall photography dream, cyclists paradise, star gazing/campfire, hiking, kayaking, canoeing, fly fishing, Frank Lloyd Wright, WI Dells and other local attractions. The home was completely renovated with all the modern conveniences but the Farmhouse charm. A sleeping loft adds additional functionality.

Guest favorite

A well-lit living area features hardwood floors and classic wooden doors. A small table is surrounded by two chairs, with a vintage lamp providing soft lighting. Artwork adorns the walls, adding character to the inviting space.

Apartment in Hillsboro

4.88 out of 5 average rating, 104 reviews

The Shopkeeper's Apartment in Yuba

The Shopkeeper’s Apartment in Yuba is the lower rear apartment in a 4-unit commercial brick building. The historically renovated space has a mix of old and new, with hardwood floors, a few restored wooden windows, and a full kitchen and bathroom with a walk-in shower. 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. Most days, you can grab a drink and meal next door at Louie's Bar.

Guest favorite

The bedroom features a spacious bed dressed in navy bedding, complemented by decorative pillows. A bedside table with a lamp is positioned next to the bed. Natural light filters through a window adorned with dark curtains, while a framed landscape art piece decorates the wall.

Home in Richland Center

4.9 out of 5 average rating, 119 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.

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

4.95 out of 5 average rating, 207 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, 269 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!

Top guest favorite

A scenic view of the earthen house is framed by lush grass and trees, with a gravel path leading towards the entrance. The cabin's exterior showcases earthy tones blending with the natural landscape, providing a serene atmosphere in the surrounding valley.

Earthen home in Ontario

4.95 out of 5 average rating, 108 reviews

Straw Clay Cabin on a Sustainable Farm

This Earthen house is made of sand, straw and clay. Nestled in a valley it is a peaceful and unique getaway. The cabin has four comfortable single beds and electricity, a wood stove for winter. Outside a fire pit and grill. A hand washing sink inside; and port-o-let toilet outside. You may be able to drive in (weather/road condition depending). It is a short walk to our Bakery (Sat. 9 am until 2 pm) Please arrive before dark. We are LGBTQ owned and operated. BIPOC welcome.

Guest favorite

A well-appointed interior space features a cozy sleeping area with a light-colored bed and natural wood accents. A small dining table is set with plates and candles, while a comfortable seating area includes a leather couch adorned with a green throw pillow. Large windows offer views of the surrounding woods.

Tiny home in Elroy

4.97 out of 5 average rating, 167 reviews

Emerald Little Lodge Overlooking Woodland Pond

Check out Opal Little Lodge also! - - - - - - - - - - - - - - - - - - - - - This cozy modern little lodge designed and built by Wisconsin Tiny Homes, is tucked into the woods 150 ft above a small woodland pond in the valley below. A bird lover's paradise. Comfortably and thoughtfully appointed, it's the perfect getaway to enjoy with a companion or as a solo retreat. Immerse yourself in nature and treat yourself with luxurious accommodations and private hiking trails.

Top guest favorite

The fully equipped kitchen features wooden cabinetry and a double sink, with gray countertops providing ample workspace. A stainless steel refrigerator stands adjacent to the microwave. In the background, the inviting living area is visible, showcasing comfortable seating and ambient lighting.

Loft in Richland Center

4.96 out of 5 average rating, 107 reviews

Downtown Loft

This lovely, fully furnished loft is downtown Richland Center. The perfect place for a professional to live when in southwest Wisconsin on a 1-12 month business assignment. It's furnishings include a quiet patio outback with an outdoor dining area, queen sized bed in bedroom, plenty of closet space, fully functioning kitchen, washer/dryer, clean, updated, and just a short walk to the espresso shop, Occooch Books & libations, as well as other shopping and restaurants.

Top guest favorite

A two-story house features a white exterior with green trim, including a covered front porch with seating. A balcony is visible on the second floor above the porch. Lush green grass surrounds the home, with trees providing shade in the background.

Home in Wilton

4.99 out of 5 average rating, 140 reviews

Cozy Three Bedroom House

Relax while you enjoy slow living in the peaceful town of Wilton. There are plenty of activities and places to see nearby if you’d like to get out and enjoy the small town atmosphere. Sparta Elroy Bike Trail (Just down the road) Wildcat Mountain (11 Miles) Wisconsin Dells (60 Miles) Canoeing/Tubing/Kayaking on the Kickapoo (8 Miles) Things to Do/Check Out: Friday Night Fish Frys Tractor Pulls Cheese Stores/Creamerys Horseback Riding Fishing

Top guest favorite

A cozy living area showcases a grey sofa and a patterned armchair, complemented by a wooden coffee table. Soft lighting is provided by two table lamps, and the space features wooden floors with area rugs. An archway leads to the adjoining kitchen area.

Apartment in Wonewoc

4.96 out of 5 average rating, 282 reviews

Winding River Air BnB

We offer a private upstairs furnished AirBnB overlooking Wonewoc's business district. One queen bedroom, queen sofa sleeper, open kitchen, dining, and living area with Smart TV and WIFI. Winding River is located mid point of the 400 State Bike Trail and 40 minutes from Wisconsin Dells. Wonewoc is a small rural farming community on picturesque Hwy 33 between Madison and LaCrosse.along the Baraboo River.