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Search results; Over 1,000 homes in Hillsboro

Top guest favourite
Home in Hillsboro
Explore 80 Acres • Cozy, Pet-Friendly Home
3 bedrooms, 5 beds, 1.5 shared bathrooms
26–31 Jul
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4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Hillsboro
Hillsboro Driftless Guesthouse is cozy for you!
4.98 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
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Townhouse in Hillsboro
Spacious Hillsboro Condo
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
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Home in Hillsboro
The Brewery House
5.0 out of 5 average rating, 28 reviews, 5 bedrooms, 11 beds, 3.5 bathrooms
31 Aug – 5 Sept
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Home in Union Center
Charming country home - great vacation area.
4.99 out of 5 average rating, 137 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Cabin in Hillsboro
Wood Heaven Hideaway
4.93 out of 5 average rating, 126 reviews, 1 bedroom, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Home in Hillsboro
Driftless Area Hidden Hollow House
4.93 out of 5 average rating, 111 reviews, 3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
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Flat in Wonewoc
Winding River Air BnB
4.96 out of 5 average rating, 308 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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Farm stay in Wilton
Dorset Valley Trailside Inn
5.0 out of 5 average rating, 24 reviews, 6 bedrooms, 8 beds, 6 bathrooms
10–15 Aug
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Home in La Farge
V's Rockton Top Getaway
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
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Flat in Wonewoc
202 Center Street Suite *30 min from Wis. Dells
5.0 out of 5 average rating, 62 reviews, 2 bedrooms, 4 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Tiny home in Yuba
The tiny house getaway by the Kickapoo reserve
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
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Home in Viola
TerraVista House in Driftless Wisconsin
4.99 out of 5 average rating, 156 reviews, 7 bedrooms, 12 beds, 3 bathrooms
6–11 Jul
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Home in Richland Center
A Piece of Heaven
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Cabin in Kendall
Spring Bank Cabin
4.94 out of 5 average rating, 125 reviews, 2 bedrooms, 4 beds, 1 bathroom
6–11 Jul
Cabin in Richland Center
South Buck Ridge
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Home in Ontario
Broken Windmill Inn Ontario Farm Retreat
4.96 out of 5 average rating, 51 reviews, 4 bedrooms, 8 beds, 2 bathrooms
12–17 Jul
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Cabin in Hillsboro
Naturesong Retreat
4.93 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
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Cottage in Ontario
Cozy stay at base of Wildcat Mt- Driftless Hygge!
4.99 out of 5 average rating, 151 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul