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Search results; Over 1,000 homes in Kendall

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Top guest favourite
Tent in Kendall
Driftless Glamping on a Bluff
1 bedroom, 0.5 private bathroom
20–25 Sept
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4.91 out of 5 average rating, 150 reviews
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Superhost
Home in Camp Douglas
GrandBadgerResort - Indoor Pool/Golf Sim/Sleeps 30
6 bedrooms, 19 beds, 8 bathrooms
1–6 Oct
New place to stay
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Home in Elroy
Relaxation Ridge
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Oct
New place to stay
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Home in Elroy
Little House on the Trail.
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
New place to stay
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Guest favourite
Farm stay in Wilton
Dorset Valley Trailside Inn
6 bedrooms, 7 beds, 6 bathrooms
11–16 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Flat in Wonewoc
202 Center Street Suite *30 min from Wis. Dells
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 71 reviews
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Guest favourite
Home in Ontario
Broken Windmill Inn Ontario Farm Retreat
4 bedrooms, 8 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 54 reviews
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Top guest favourite
Home in New Lisbon
The Pickle Barn - Indoor Pickleball & Basketball
6 bedrooms, 14 beds, 5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Hillsboro
The Brewery House
5 bedrooms, 11 beds, 3.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Union Center
Charming country home - great vacation area.
3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 147 reviews
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Top guest favourite
Campsite in Kendall
Driftless Bluff Glamping Cabin, Peaceful, Secluded
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 166 reviews
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Top guest favourite
Tiny home in Elroy
Emerald Little Lodge Overlooking Woodland Pond
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 199 reviews
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Guest favourite
Cabin in Forest
Driftless Trout Cabin - Hillsboro, Wisconsin
2 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 201 reviews
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Guest favourite
Bungalow in Wonewoc
Colorful getaway in friendly Driftless village
3 bedrooms, 3 beds, 1 bathroom
18–23 Sept
4.89 out of 5 average rating, 91 reviews
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Top guest favourite
Tiny home in Ontario
Maggie's Place at Echo Valley Farm
2 single beds, WC
18–23 Sept
4.91 out of 5 average rating, 151 reviews
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Top guest favourite
Home in Hillsboro
Hillsboro Driftless Guesthouse is cozy for you!
2 bedrooms, 3 beds, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 98 reviews
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Home in La Farge
Rockton Retreat: Your Driftless Kickapoo Getaway
2 bedrooms, 6 beds, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Necedah
Mini Cabin in the Woods. BRAND NEW BUILD in 2026.
2 bedrooms, 2 beds, 2 bathrooms
23–28 Sept
New place to stay
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Guest favourite
Cabin in Norwalk
Vista View Mini Cabin | Porch Views & Cozy Loft
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews