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Guesthouse vacation rentals in Wisconsin

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Top-rated guesthouse rentals in Wisconsin

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Mount Horeb
Cool, Scenic Country Art Studio
Creative souls love my marvelous studio retreat, a delightful space that features tall ceilings and an open design--giving it a loft feel with an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs included in your online reservation, must be leashed when outside, and kenneled in your absence.
Mar 22 – 29
$91 per night
Guest favorite
Guesthouse in Wisconsin Dells
Waterfront Cottage with beautiful views
This waterfront cottage has beautiful views of the Wisconsin River. My husband and I have lived here for more than 20 years. We love this area - there is nothing like a cool, crisp Midwest morning overlooking the Wisconsin River. Or enjoying a great glass of wine (or Wisconsin beer) while watching a spectacular summer sunset from the deck. Expect peace and tranquility as we are far enough from Downtown Dells to avoid the crowds and noise. We look forward to hosting you and your loved ones.
Apr 23 – 30
$56 per night
Guest favorite
Guesthouse in Ontario
Rustic Spring Cabin at Echo Valley Farm
Next to a spring and gardens. Simple glamping with electricity, wood burning stove and water. Grill and fire pit available. Parking for 1 car at the cabin. Non chemical port-o-let toilet is a short walk. 3 miles from Wildcat Mountain State Park and 7 miles from the Kickapoo Valley Reserve. Great for hiking, getting "unhooked" and back to Nature. This cabin is located near another farm resident's cabin. Bakery's open on Sat.Sun, May - October or order in advance in off season. LGBTQ owned.
Mar 1 – 8
$65 per night

Popular amenities for Wisconsin guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Cashton
Enjoy your space at the Mielke Way!
Mar 29 – Apr 5
$74 per night
Guest favorite
Guesthouse in Viroqua
The Country Loft
Apr 15 – 22
$86 per night
Guest favorite
Guesthouse in Elkhorn
Camp Wandawega: Lakeview 3 Bedroom Cabin
Mar 12 – 17
$650 per night
Guest favorite
Guesthouse in Hudson
Cottage in historic Hudson, 5 blocks from DT
Dec 4 – 11
$113 per night
Guest favorite
Guesthouse in Earl
Earl Eddy
Apr 1 – 8
$165 per night
Guest favorite
Guesthouse in Oshkosh
Cottage on Lake Winnebago
Mar 26 – Apr 2
$135 per night
Guest favorite
Guesthouse in Milwaukee
Cozy Brewer's Hill Coach House
Aug 16 – 23
$91 per night
Guest favorite
Guesthouse in Hubertus
Quiet retreat-golf, bike, hike, motorcycle
Sep 9 – 16
$167 per night
Guest favorite
Guesthouse in Milwaukee
The Carriage House in Sanger House Gardens
Nov 3 – 10
$121 per night
Guest favorite
Guesthouse in Spooner
Secluded Northwoods Cabin
Jun 12 – 19
$238 per night
Guest favorite
Guesthouse in Kaukauna
Country Sky Private Guest House (3 bedroom 1 Bath)
Jun 12 – 19
$221 per night
Guesthouse in Viroqua
Eagle's Nest Cabin at Earthology Retreat Center
Jun 27 – Jul 4
$62 per night

Guest house rentals with a patio

Guest favorite
Guesthouse in Fish Creek
Vintage Mod Cottage with fireplace & soaking tub!
Oct 30 – Nov 6
$208 per night
Guest favorite
Guesthouse in Gays Mills
The Bunkhouse on 80 acres, trails
Jul 18 – 25
$72 per night
Superhost
Guesthouse in Ashland
Beach Front Hideaway
Jan 6 – 13
$212 per night
Guest favorite
Guesthouse in Elk
Beautiful one bedroom carriage house
Jun 17 – 24
$110 per night
Guest favorite
Guesthouse in Solon Springs
Highland Hideaway
Jun 13 – 20
$100 per night
Guest favorite
Guesthouse in West Bend
Wilderness Retreat*Private Deck*Gazebo*Fireplace
Nov 20 – 27
$162 per night
Guest favorite
Guesthouse in Washburn
Glamping Cabin at Whitecap Kayak Learning Center
Mar 5 – 12
$89 per night
Guest favorite
Guesthouse in Mequon
Historic 1-bedroom guesthouse w/ indoor fireplace
Dec 13 – 20
$152 per night
Guest favorite
Guesthouse in Marshfield
Sunset Suite
$62 per night
Guest favorite
Guesthouse in Hayward
The Brook Cottage
Nov 27 – Dec 4
$110 per night
Guest favorite
Guesthouse in Superior
Studio Apartment on St. Louis River
Mar 26 – Apr 2
$90 per night
Guest favorite
Guesthouse in Ojibwa
Club Suite Recreational Retreat
Jul 26 – Aug 2
$120 per night

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Ashland
Norrsken Scandinavian Cottage
Sep 27 – Oct 4
$161 per night
Guest favorite
Guesthouse in Cornucopia
Waterfront Lake Superior's South Shore, "Sky Fire"
May 24 – 31
$279 per night
Guest favorite
Guesthouse in Hixton
Country Retreat. Beautiful sunsets and sunrises.
Jul 22 – 29
$122 per night
Guest favorite
Guesthouse in Madison
Historic guesthouse near downtown, hospital and UW
Jul 24 – 31
$143 per night
Guest favorite
Guesthouse in Land O' Lakes
North Woods Pristine Lake Paradise!
Jan 13 – 20
$102 per night
Guest favorite
Guesthouse in Three Lakes
Above the Books--2 bedroom Apartment
Apr 18 – 25
$83 per night
Superhost
Guesthouse in Stevens Point
Cozy Cabin in the Woods
May 3 – 10
$112 per night
Guest favorite
Guesthouse in Westby
The Honey Haven
Mar 16 – 23
$152 per night
Guest favorite
Guesthouse in Baileys Harbor
Lighthouse Lookout
Aug 11 – 18
$226 per night
Guest favorite
Guesthouse in Shorewood
Adorable Upper Bungalow Retreat
Apr 1 – 8
$150 per night
Guest favorite
Guesthouse in Bayfield
Seclusion in the Pines - A Hidden Gem in Bayfield
Apr 23 – 30
$295 per night
Guest favorite
Guesthouse in Drummond
Bearadise a Secluded get-away.
Apr 25 – May 2
$264 per night

Destinations to explore