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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
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, 101 reviews
Campsite in Spring Green
Romantic & Fun Glamping at Wilson Creek Getaway
1 queen bed, No bathroom
13–18 Aug
4.88 out of 5 average rating, 17 reviews
Top guest favourite
Cabin in Boscobel
Crooked Creek - Relaxation Cabin
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 94 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
Guest favourite
Guest suite in Spring Green
River Valley Retreat
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.8 out of 5 average rating, 242 reviews
Top guest favourite
Home in Hillsboro
Driftless Area Hidden Hollow House
3 bedrooms, 6 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 117 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
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, 290 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, 117 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 Mount Horeb
Unique 1860's Stone House Rural Retreat for Gals!
1 double bed, 1.5 bathrooms
21–26 Aug
4.94 out of 5 average rating, 290 reviews
Guest favourite
Cabin in Baraboo
Fireside Cabin 8 | Baraboo • Dells Cabin | Pets OK
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 32 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, 125 reviews
Top guest favourite
Home in Baraboo
Cottage Near Devil's Lake
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 166 reviews
Room in Reedsburg
Stay Near 400 Trail | Free Breakfast & Parking
2 queen beds, 1 bathroom
11–16 Aug
4.27 out of 5 average rating, 22 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
Guest favourite
Cabin in Ontario
Driftless Ridge Glamping Retreat | Cozy + Scenic
1 bedroom, 1 queen bed, WC
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Richland Center
Local Charm at Natures Door
3 bedrooms, 5 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 61 reviews