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Search results; Over 1,000 homes in Plain

Top guest favourite
Farm stay in Plain
Grateful Farms Cabin: Hills, Creek, Gorgeous Views
1 bedroom, 2 beds, 1 private bathroom
17–22 Aug
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4.95 out of 5 average rating, 245 reviews
Campsite in Spring Green
Romantic & Fun Glamping at Wilson Creek Getaway
1 queen bed, No bathroom
14–19 Aug
4.88 out of 5 average rating, 17 reviews
Guest favourite
Camper van/Motorhome in Cross Plains
Farm Chic Vintage Camper
1 bedroom, 1 bed, 1 bathroom
29 Apr – 4 May
4.9 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in Belleville
Still Point Tiny House - (Zero Added Cleaning Fee)
1 bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 291 reviews
Top guest favourite
Earthen home in Spring Green
Forest Retreat in Earth Home 10 Min from APT
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 102 reviews
Guest favourite
Cabin in Boscobel
Crooked Creek - Rustic Cabin
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.86 out of 5 average rating, 107 reviews
Guest favourite
Room in Wisconsin Dells
Juniper Motel & Resort: Double Queen
2 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 61 reviews
Guest favourite
Flat in Baraboo
Orchard Prairie B&B
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 309 reviews
Tiny home in La Farge
Driftless Tiny House Retreat
1 bedroom, 2 beds, WC
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Guest suite in Loganville
Village Cozy Suite
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 118 reviews
Top guest favourite
Tiny home in Yuba
The tiny house getaway by the Kickapoo reserve
1 bedroom, 2 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Hillsboro
Hillsboro Driftless Guesthouse is cozy for you!
2 bedrooms, 3 beds, 1 bathroom
18–23 Aug
4.98 out of 5 average rating, 91 reviews
Top guest favourite
Tiny home in Richland Center
Walnut Cabin w/Sauna-Dog Friendly
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 211 reviews
Top guest favourite
Home in Madison
Historic guesthouse near UW
1 bedroom, 1 bed, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 58 reviews
Top guest favourite
Camper van/Motorhome in Hill Point
Big R’s Retreat 2 Secluded with HOT TUB
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 173 reviews
Top guest favourite
Tiny home in Richland Center
Dog-Friendly Mighty Pine Cabin Escape w/Sauna
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
4.98 out of 5 average rating, 127 reviews
Top guest favourite
Cabin in Muscoda
Riverview Cabin, LLC
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Room in Baraboo
The Driftless Doorway
1 single bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Flat in Avoca
Farm in the Driftless | Private + Family-Friendly
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 21 reviews