Guesthouse holiday rentals in Wisconsin
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Top-rated Guesthouses in Wisconsin
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Wisconsin guesthouses
Family-Friendly guesthouses
Guesthouse in Viroqua
4.87 out of 5 average rating, 224 reviewsThe Country Loft
21–28 Apr
Guesthouse in Cashton
4.97 out of 5 average rating, 310 reviewsEnjoy your space at the Mielke Way!
31 Jan – 7 Feb
Guesthouse in Oshkosh
4.95 out of 5 average rating, 170 reviewsCottage on Lake Winnebago
1–8 Jun
Guesthouse in Milwaukee
4.95 out of 5 average rating, 246 reviewsThe Carriage House in Sanger House Gardens
20–27 Apr
Guesthouse in Hudson
4.96 out of 5 average rating, 165 reviewsCottage in historic Hudson, 5 blocks from DT
30 Sep – 7 Oct
Guesthouse in Milwaukee
4.86 out of 5 average rating, 274 reviewsCozy Brewer's Hill Coach House
11–18 Jan
Guesthouse in Hubertus
4.96 out of 5 average rating, 137 reviewsQuiet retreat-golf, bike, hike, motorcycle
19–26 Dec
Guesthouse in Elkhorn
4.98 out of 5 average rating, 145 reviewsCamp Wandawega: Lakeview 3 Bedroom Cabin
4–9 Sep
Guesthouses with a patio
Guesthouse in Lake Nebagamon
5.0 out of 5 average rating, 15 reviewsCozy & Charming Guesthouse
20–27 Jan
Guesthouse in Gays Mills
5.0 out of 5 average rating, 56 reviewsThe Bunkhouse on 80 acres, trails
13–20 Nov
Guesthouse in Solon Springs
5.0 out of 5 average rating, 31 reviewsHighland Hideaway
24 Nov – 1 Dec
Guesthouse in West Bend
5.0 out of 5 average rating, 60 reviewsWilderness Retreat*Private Deck*Gazebo*Fireplace
25 Aug – 1 Sep
Guesthouse in Kaukauna
4.94 out of 5 average rating, 36 reviewsA Sweet Suite in Freedom! Country Comfort!
12–19 Jul
Guesthouse in Elk
4.98 out of 5 average rating, 45 reviewsBeautiful one bedroom carriage house
31 Dec – 7 Jan
Guesthouse in Superior
4.97 out of 5 average rating, 61 reviewsStudio Apartment on St. Louis River
17–24 Oct
Guesthouse in Hayward
4.96 out of 5 average rating, 25 reviewsThe Brook Cottage
2–9 Feb
Guest house rentals with a washing machine and dryer
Guesthouse in Cornucopia
4.9 out of 5 average rating, 265 reviewsWaterfront Lake Superior's South Shore, "Sky Fire"
19–26 Dec
Guesthouse in Hixton
4.96 out of 5 average rating, 102 reviewsCountry Retreat. Beautiful sunsets and sunrises.
14–21 May
Guesthouse in Madison
4.92 out of 5 average rating, 246 reviewsHistoric guesthouse near downtown, hospital and UW
14–21 Sep
Guesthouse in Hayward
5.0 out of 5 average rating, 105 reviewsSilent Sports Retreat in Seeley
24–31 Oct
Guesthouse in Land O' Lakes
4.92 out of 5 average rating, 60 reviewsNorth Woods Pristine Lake Paradise!
4–11 Apr
Guesthouse in Ladysmith
5.0 out of 5 average rating, 15 reviewsThe Bunkhouse, a Northwoods Escape
11–18 Dec
Guesthouse in Hudson
4.9 out of 5 average rating, 61 reviewsStay in the shed
28 Sep – 5 Oct
Guesthouse in Egg Harbor
5.0 out of 5 average rating, 21 reviewsVillage Tree House, chill setting walkable to town
24–31 Dec
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