A forested river with clear water reflecting trees and rocky cliffs.

Holiday Homes in Hillsboro

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Hillsboro holiday homes

A living room with a television, a coffee table, a sofa, and a dining area in the background.

1. 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, (29 reviews)
"Nice place just outside city limits. Good spot to check out the area."
United States
Dan G.
The price is NZ$374
includes taxes & fees
5 Oct - 6 Oct
Hillsboro Driftless Guesthouse is cozy and ready for you!
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

2. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (15 reviews)
"Sweet home! Loved all the bright colored decorations! We had a great stay here with our bikes and pups. The porch was lovely to watch a thunderstorm from as well!"
United States
Emily B.
The price is NZ$464
includes taxes & fees
30 Sept - 1 Oct
Colorful getaway in friendly Driftless village
A two-story house with a balcony, surrounded by a forest.

3. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
10.0 out of 10, Exceptional, (12 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is NZ$631
includes taxes & fees
5 Oct - 6 Oct
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
A modern kitchen with a large island, white cabinetry, a microwave, and a sink.

4. Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
Reedsburg
9.8 out of 10, Exceptional, (17 reviews)
"The home was very comfortable and clean. It had everything we needed and we would definitely stay here again! "
United States
Ken M.
The price is NZ$896
includes taxes & fees
30 Sept - 1 Oct
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
Living Room | Twin Sleeper Sofa

5. 12 Mi to Castle Rock Lake: Serene New Lisbon Home!

12 Mi to Castle Rock Lake: Serene New Lisbon Home!
New Lisbon
10.0 out of 10, Exceptional, (4 reviews)
"Dated furnishing but clean, neat a n and well cared for. Handy location. Great hosts"
United States
nick k.
The price is NZ$714
includes taxes & fees
23 Oct - 24 Oct
12 Mi to Castle Rock Lake: Serene New Lisbon Home!
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

6. 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
9.0 out of 10, Wonderful, (18 reviews)
"excellent out of the way retreat close to things we wanted to do and great place for us and our cats, the hot tub was a great treat"
United States
Joseph W.
The price is NZ$536
includes taxes & fees
30 Sept - 1 Oct
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

7. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (62 reviews)
"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."
United States
Eric R.
The price is NZ$438
includes taxes & fees
19 Oct - 20 Oct
The Honey Haven
A dining area with a wooden table, white chairs, and a chandelier.

8. Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Cashton
9.6 out of 10, Exceptional, (4 reviews)
"Was in town for a wedding, it was a comfortable place. The master bedroom bed was comfortable and everything was very clean."
United States
Catherine T.
The price is NZ$616
includes taxes & fees
30 Sept - 1 Oct
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
A covered deck with outdoor furniture, a small table, and a grill.

9. Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.6 out of 10, Exceptional, (34 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is NZ$1,231
includes taxes & fees
6 Oct - 7 Oct
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
A spacious kitchen with wooden cabinets, a central island with stools, a dining area with a round table and chairs, and a ceiling fan.

10. 6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (26 reviews)
"It’s the good house and all the bed rooms have attached bathroom. Suggest to the homeowner is that keeping the bath shower and moisturizer at each room"
United States
Rambabu
The price is NZ$1,229
includes taxes & fees
1 Oct - 2 Oct
6 Bedroom Home in Gods Country
A cozy living room with a wooden ceiling, a grey sofa, and a view through a glass door to an outdoor patio.

11. Secluded Rustic Cabin

Secluded Rustic Cabin
Cashton
9.8 out of 10, Exceptional, (59 reviews)
"What a wonderful property! "
United States
Becky K.
The price is NZ$880
includes taxes & fees
30 Sept - 1 Oct
Secluded Rustic Cabin
A modern kitchen with a white countertop, a black and white tiled backsplash, and a stainless steel oven.

12. KwikStay: The Small-Town Ranch Style Home

KwikStay: The Small-Town Ranch Style Home
Loganville
10.0 out of 10, Exceptional, (6 reviews)
"Home was absolutely beautiful with plenty of room for everyone. Centrally located to all attractions, with short travel times. Host was amazing to work with. "
United States
Dawn B.
KwikStay: The Small-Town Ranch Style Home
A wooden cabin-style kitchen with granite countertops, wooden cabinets, a dishwasher, and a built-in stove.

13. Revilo Moose Ridge Mauston - Smoky Mt Vibes, Wisconsin Wild

Revilo Moose Ridge Mauston - Smoky Mt Vibes, Wisconsin Wild
Mauston
10.0 out of 10, Exceptional, (3 reviews)
"We celebrated my wife's 40th birthday there with friends.They had everything we needed and more. Paul was great and quick to respond.I would definitely stay there again!"
United States
Darius L.
The price is NZ$1,498
includes taxes & fees
1 Oct - 2 Oct
Revilo Moose Ridge Mauston - Smoky Mt Vibes, Wisconsin Wild
A modern living room with a large window, a sofa, a coffee table, and a chair.

14. “The Ridgeline” – Luxury private home, on 4 acres

“The Ridgeline” – Luxury private home, on 4 acres
Viroqua
The price is NZ$648
includes taxes & fees
18 Oct - 19 Oct
“The Ridgeline” – Luxury private home, on 4 acres
A grand staircase with a chandelier, a large rug, and a view into the living area.

15. Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+

Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+
Camp Douglas
The price is NZ$4,392
includes taxes & fees
21 Oct - 22 Oct
Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+
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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