Places to stay in Hillsboro

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Top-rated places to stay in Hillsboro

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

A rustic cabin exterior is illuminated under the night sky, with warm light glowing from the windows. A fire pit is centrally located, surrounded by two wooden Adirondack chairs. The porch features a welcoming swing and potted plants for added charm.

Cabin in Hill Point

4.97 out of 5 average rating, 541 reviews

Big R's Retreat Secluded and located in Nature

Welcome to our home: where we have found peace and relaxation for over 20 years. A German native, Big R fell in love with the open land and rolling hills of Wisconsin, becoming a US citizen in the 80s. He met Curly, a Chicago city girl, who brought a little city to his country life. They enjoy raising buffalo and spending warmer days on their porch enjoying the fresh air and beautiful views (with no mosquitos!). Now they want to share their idyllic and peaceful home with you. Drive down a dead-end road and pull up to a rustic cabin filled with high-tech and cozy amenities. We have something for everyone with a gas fireplace, tv (complete with dish, Cinemax, HBO and a Bluetooth sound system), board games and a full kitchen. Take a drink outside to soak in the hot tub or sit around the campfire. When the day is done, you will fall asleep instantly on the memory foam bed, either in the loft or the bedroom, and wake up to a beautiful sunrise looking out over your little getaway.

Top guest favorite

Home in La Farge

4.97 out of 5 average rating, 185 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, 109 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.

Guest favorite

Cabin in Forest

4.97 out of 5 average rating, 153 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

Guest favorite

A securely closed bank vault door leads into a dimly lit, concrete-enclosed space. A single light bulb hangs from the ceiling, illuminating the rough walls. The door, finished in gray, features multiple locks and hinges, emphasizing its historical significance.

Apartment in Hillsboro

4.95 out of 5 average rating, 110 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

Bungalow in Richland Center

5 out of 5 average rating, 299 reviews

GloryView 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.

Top guest favorite

An outdoor seating area is illuminated by strings of lights under a wooden pergola. The space features a stone patio with several wooden benches and a fire pit, surrounded by open grass and a white fence in the background.

Home in Richland Center

4.95 out of 5 average rating, 258 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

An inviting interior showcases a blend of natural materials. A red seating area is complemented by a wooden dining table and chairs. Soft lighting filters through two windows, creating a warm ambiance. A wood stove anchors the space, enhancing the cabin's rustic charm.

Earthen home in Ontario

4.95 out of 5 average rating, 102 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 cozy lodge emerges amidst a quiet snowy landscape. Snow blankets the ground and branches of trees, while warm lights glow softly from the windows. Two benches are positioned nearby, inviting guests to enjoy the serene winter scenery.

Tiny home in Elroy

4.97 out of 5 average rating, 155 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.

Guest favorite

Tent in Kendall

4.89 out of 5 average rating, 114 reviews

Driftless Glamping on a Bluff

Rustic camping in the Driftless Region on the top of a bluff in a 20ft. Bell Tent. Relax, without having to pack, set up camp, and tear down and put away when you get home, more time to do things you enjoy. Go trout fishing, walk or ride the Omaha Trail Tunnel, Elroy- Sparta Trail, or the 400 Trail. Necedah Wildlife Refuge, Buckhorn, Castle Rock, Wisconsin Dells, Amish scenic drive, and Wildcat State Park with canoeing down the Kickapoo River are all within 30 minutes.

Top guest favorite

A spacious shower is enclosed in a clear glass stall, featuring built-in shelves for toiletries. Soft, neutral tones dominate the room's decor, complemented by neatly arranged towels stacked on a wooden bench. A small window allows natural light to enter, enhancing the overall brightness.

Home in Union Center

4.99 out of 5 average rating, 108 reviews

Charming country home - great vacation area.

This attractive, peaceful country home is nearby to many family tourist attractions: including Wisconsin Dells, Lake Redstone Park, Elroy-Sparta Bike Trail, fishing, hiking, and canoeing. Provisions for a simple country breakfast are included in your stay. This newly remodeled home with a 2 story layout provides plenty of room for up to 7 guests. Large backyard includes a firepit, as well as a view of the adjacent golf course. Large driveway to park in.

Top guest favorite

An open kitchen area features wooden cabinetry and a contrasting dark refrigerator. A variety of kitchen appliances, including a microwave, are present on the shelves. The space is complemented by a cozy living area with a patterned armchair and a wooden coffee table.

Apartment in Wonewoc

4.96 out of 5 average rating, 272 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.

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Other great vacation rentals in Hillsboro

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Loft in Wonewoc

4.83 out of 5 average rating, 83 reviews

1st Flr Studio Apt Sleeps 12 in Historic Feed Mill

JustinRating, 5 stars6 months ago

A great, cozy place to stay, especially if you have kid's. The kid's absolutely loved hanging out in the loft.

Top guest favorite

Cabin in Baraboo

5 out of 5 average rating, 15 reviews

SamanthaRating, 5 stars1 week ago

My two best friends and I stayed at the fabulous Refugio Graziella for a relaxing girls’ weekend and it. was. perfect. Most of the weekend was spent lounging and chatting in all the many wonderful spaces the home offers: sipping coffee on the peaceful screened-in porch, relaxing in the hot tub, roasting marshmallows at the serene fire pit under the string lights with ample firewood and supplies, doing crafts and playing games at the inviting dining room table, cooking meals in the fully equipped kitchen, and listening to music in the cozy living room. We did not end up using the sauna (just didn’t have time), but are already planning a winter getaway to RG. We absolutely loved our stay and highly recommend it if you are looking for a quiet getaway, surrounded by nature but still a short drive away from anything you need or want. Clearly, so much thought was put into anticipating the needs of their guests, and that makes Refugio Graziella a place you immediately feel comfortable. 🥰

Top guest favorite

A horse-drawn black buggy is seen moving along a rural road under a partly cloudy sky. The surrounding landscape features open fields and trees, enhancing the serene atmosphere of the area.

Home in Hillsboro

4.98 out of 5 average rating, 51 reviews

Spacious home with no pet fees on 80 acres

MaximilianRating, 5 stars5 days ago

We had a great stay at Joanne’s home. The place was super clean, peaceful, and perfect for a few days away. We spent most of our time outside with our dogs, hiking nearby trails, kayaking, and just enjoying the quiet. It felt like a nice little escape. Would definitely come back!

Guest favorite

Bungalow in Wonewoc

4.88 out of 5 average rating, 84 reviews

Colorful getaway in friendly Driftless village

LauraRating, 5 stars1 month ago

Great location, walking distance to the downtown area that includes a great market, flower shop and taverns that serve food. Isaac has a well stocked kitchen with everything you need! Loved sitting in the sunroom in the morning and the porch at night. The residents of Wonewoc are very welcoming. We loved the breakfast at the Wonewoc Legion Hall on Sunday.

Top guest favorite

An inviting interior features wooden walls and warm lighting. A dining table with several chairs occupies the center, while a kitchen area with modern appliances is situated on one side. A decorative sign hangs above, contributing to the cabin's welcoming ambiance.

Cabin in Ontario

4.99 out of 5 average rating, 76 reviews

Hill Top Hideaway

MariahRating, 5 stars2 weeks ago

We had an amazing stay at the cabin. It was so peaceful and secluded. Loved being able to have our dogs with us on this trip as well. We were able to enjoy a fire on our first night and grilled on the second night. We also kayaked the Kickapoo river which was only a few miles from the cabin. We will definitely be back very soon.

Guest favorite

A blue cabin is positioned on a gravel area surrounded by green grass. A picnic table sits in front, while a fire pit with two chairs is located nearby. The scene is illuminated by warm sunlight, highlighting the rustic charm of the setting.

Tiny home in Norwalk

4.98 out of 5 average rating, 41 reviews

Repurposed, rustic and tranquil tiny home #1

BrettRating, 5 stars1 week ago

Peaceful retreat to get away! Very clean and fresh cabin. I highly recommend to anyone getting away from the hustle and bustle!

Guest favorite

A covered porch provides a view of a tranquil pond surrounded by lush greenery. A bird feeder is visible, with an inviting grassy area leading to the water's edge, enhancing the connection with nature.

Cabin in Ontario

4.94 out of 5 average rating, 48 reviews

Brush Creek Hideaway

TraciRating, 5 stars1 week ago

It is one of the loveliest Air BnB places I have stayed in. Barb is a great host and very helpful and friendly. The cabin was beautifully decorated and the grounds are so beautiful and well tended. Absolutely Lovely. The only issue we had was with phone service (no Verizon coverage) and no WiFi available. Recommend downloading your maps and Barb’s directions before you get to Ontario. None of this was the host’s fault and does not detract from the overall beauty and charm of the place. We loved it. Will be back!

Top guest favorite

An open-concept space features high ceilings with wooden beams and large windows allowing natural light to flood the area. A spacious kitchen island with a dark countertop stands at the center, surrounded by dining seating. Adjacent, a cozy seating area is visible, complemented by a modern fireplace.

Cabin in Blue River

5 out of 5 average rating, 20 reviews

New Secluded Cabin Quiet Getaway

PawelRating, 5 stars1 week ago

Great! Amazing! Beautiful! I would give even ten stars if this would be possible. House located in very stunning and peaceful area, perfect for getaway! Just nature and you! House itself its very clean and well finished, pretty much everything that you need its in there! And host is taking care of everything above and beyond! Can’t wait to visit again! Definitely recommend this house, listing and host! It was a pure pleasure to spend a time there. Thank you Corey!

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Places to stay in Hillsboro

Top-rated places to stay in Hillsboro

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