Guesthouse vacation rentals in Wisconsin

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Popular amenities for Wisconsin guesthouse rentals

Family-friendly guest house rentals

Guest favorite

Guesthouse in Cashton

4.97 out of 5 average rating, 328 reviews

Enjoy your space at the Mielke Way!

SarahRating, 5 stars4 days ago
Our family enjoyed our stay. We visited local Amish bakeries, compared cheese curds from local dairies, hiked the trails on the property, and spent a lot of time petting the cats and, Whisky, the dog. We were lucky that Al was loading and unloading the draft horses to give rides at the local pumpkin patch. He was very patient as we loitered around to watch and our toddler slowly warmed up to little Charlie. Thanks for that! You will be staying in the carriage house at the back of the garage and there are 3 generations on the property. At times, there were quite a few people around. Other times, everyone was off doing their own thing. We felt welcomed and able to come/go as we pleased. It’s fall in the country so there were lady bugs and extra spiderwebs, but that’s to be expected this time of year. The place was clean overall, comfortable, and cuter than the pictures.
Guest favorite

Guesthouse in Milwaukee

4.95 out of 5 average rating, 257 reviews

The Carriage House in Sanger House Gardens

Jackie Rating, 5 stars2 weeks ago
Look no further. The Carriage House is exceptional… a comfortable space with artifacts harkening back to its origins. The Gardens are spectacular… winding pathways, fountains, benches, pools, statuary. Peace, tranquility, and serenity abound. Steve is a wealth of information and willingly engages with guests. Staying at Sanger House Gardens is reason enough to come to Milwaukee!
Guest favorite

Guesthouse in Hudson

4.95 out of 5 average rating, 175 reviews

Cottage in historic Hudson, 5 blocks from DT

MichaelRating, 5 stars1 week ago
This was my second stay here. Beautiful house, wonderful location and a marvelous host. Highly recommended. Definitely high on my list if I should need an Airbnb here again.
Guest favorite

Guesthouse in Spring Green

4.94 out of 5 average rating, 109 reviews

Teacher’s Lounge

SharonRating, 5 stars1 month ago
My husband and I enjoyed our stay very much. We attend a few plays at Spring Green every year. Aaron & Dede were very cordial when I called and asked if we could check in early. The apartment was clean and well appointed. We would enjoy staying here again.
Guest favorite

Guesthouse in Maiden Rock

5 out of 5 average rating, 21 reviews

Cozy Guest House Getaway

LaurenRating, 5 stars1 week ago
We thoroughly enjoyed our stay at Danni’s place! Everything was spotless and it was very comfortable. There were very thoughtful touches including extra toiletry type items in the bathroom, coffee, creamer, snacks, and a very helpful list of local restaurants, activities and attractions! I would definitely recommend their place to anyone looking for a cozy place to stay while checking out all the little towns near Lake Pepin.
Guest favorite

Guesthouse in Earl

4.99 out of 5 average rating, 158 reviews

Earl Eddy

WendyRating, 5 stars1 month ago
We couldn’t have been happier with our stay. The home was equipped with all the necessities you may need and more, and of great quality. Fantastic communication from the host. Would love to come back when we had more time.
Guest favorite

Guesthouse in Milwaukee

4.86 out of 5 average rating, 287 reviews

Cozy Brewer's Hill Coach House

SusanRating, 5 stars2 weeks ago
A cozy and tastefully-decorated accommodation with great views of an older Milwaukee neighborhood. Close to downtown and the hip areas. Would stay again!
Superhost

Guesthouse in Pepin

4.83 out of 5 average rating, 6 reviews

Harbor Hill Inn - Carriage House

KarlynRating, 5 stars38 months ago
Rob and Jan are awesome hosts. The whole check in and check out process was seamless. The carriage house is walking distance from the harbor where we watched the sunset and is very close to restaurants and stores. We hope we are able to come stay at the Harbor Hill Carriage house again in the future!

Guest house rentals with a patio

Guest favorite

Guesthouse in Milwaukee

4.92 out of 5 average rating, 118 reviews

1-bedroom guest house with river & city views

GeorgeRating, 5 stars2 weeks ago
Melissa was very responsive to all questions. her place was very quiet and 10 minute walk to Pik and Save grocery, 10 minutes to lakefront brewery, or 18 minutes to the closest Hop stop. very safe walking area
Guest favorite

Guesthouse in Lake Nebagamon

4.89 out of 5 average rating, 37 reviews

Cozy & Charming Guesthouse

AdamRating, 5 stars2 weeks ago
If you’re looking for a great experience in the north, hard to pass this place up. A perfect location and a cozy lodging situation make this an ideal spot. 25 minutes to Duluth, and under two hours to numerous picturesque state parks; over a few days, we were able to hike five different waterfall features, and got out to the Apostle Islands for a day trip. Sunlight and deep country abound.
Guest favorite

Guesthouse in Ashland

4.9 out of 5 average rating, 40 reviews

Beach Front Hideaway

JillianRating, 5 stars1 week ago
Michelle's place is beautiful! I can imagine that it would be a stunning location in good weather - we were unlucky with rain during our stay, but it was a cozy place to be.
Guest favorite

Guesthouse in Waupaca

5 out of 5 average rating, 17 reviews

Silver Lake Studio

ElsaRating, 5 stars2 months ago
Would definitely come back. It was the perfect relaxing vacation that we needed. We felt comfortable and really enjoyed the deck and fire pit.
Guest favorite

Guesthouse in La Crosse

4.96 out of 5 average rating, 76 reviews

Mississippi River - cozy 1 bedroom

AlejandraRating, 5 stars2 weeks ago
Becky’s place was perfect for my husband, myself and our two dogs. We are so grateful that she allows dogs. While it could accommodate 4 people, I am glad it was just us. Shearing the space with another couple might have been a little awkward since there is no door on the bedroom. We really enjoyed our stay. The view of the lake is very pretty and has a big yard. I am sure this place is amazing in the summer, perfect for a family of four. We are very grateful for our time there and would recommend it to everyone.
Guest favorite

Guesthouse in Mount Horeb

5 out of 5 average rating, 13 reviews

2 bedroom condo in Mt. Horeb

BeckyRating, 5 stars2 weeks ago
Absolutely beautiful location, beautiful home, and a very sweet family. They provide everything you need. Would love to stay again.
Guest favorite

Guesthouse in Horicon

5 out of 5 average rating, 9 reviews

Boathouse Bungalow

SydneyRating, 5 stars1 month ago
This place was a great place for a weekend getaway. Very serene atmosphere and great views of the lake. The bungalow had everything you needed.
Guest favorite

Guesthouse in Manitowoc

5 out of 5 average rating, 23 reviews

Mallard Manor - Adorable 2 b/r guest house.

BryceRating, 5 stars1 week ago
Place was wonderful (As described, clean and quiet). Perfect place to stay before the Packer's game. Mari was a great host. She provided several food recommendations and even took the time to warn us about potential heavy traffic in Green Bay due to an event prior to the game. Would definitely stay again . Go Pack Go!

Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in West Bend

5 out of 5 average rating, 73 reviews

Wilderness Retreat*Private Deck*Gazebo*Fireplace

PattyRating, 5 stars1 week ago
We wanted to see Cedarburg and fall colors in Kettle Moraine but our favorite time was spent relaxing on the deck at Don and Betsy’s Wilderness Retreat! The rustling leaves and the rippling pond were super relaxing and beautiful. The guesthouse was beyond our expectations - warm, spa-like and thoughtfully equipped. Don and Betsy were wonderful. They had great restaurant suggestions in their guidebook and told us about a fun local music venue in West Bend. I’m so glad we stayed there!
Guest favorite

Guesthouse in Stratford

5 out of 5 average rating, 18 reviews

Golden Pond Cabin | Sleeps 4

EthanRating, 5 stars2 weeks ago
Loved it! Great scenery and perfect for my weekend getaway!
Guest favorite

Guesthouse in Ladysmith

4.97 out of 5 average rating, 33 reviews

The Bunkhouse, a Northwoods Escape

JackieRating, 5 stars2 weeks ago
Beautiful property! Perfect for the remote employee to escape the city for a few days. Courtney’s place is amazing. It’s quiet & peaceful with all the benefits of country life, yet less than 10 minutes from everything you might need in town. Brought our dog & enjoyed the little hiking trails right off the property. So fun & a super cozy spot! We’ll be back! 😁
Guest favorite

Guesthouse in Sturgeon Bay

4.95 out of 5 average rating, 65 reviews

Cozy 1 bedroom guesthouse with fireplace

RitaRating, 5 stars1 week ago
This was exactly what we needed for our long weekend. The home was clean and was what we expected. We appreciate Brian's clear directions and checking in with us before and during our stay. We had no issues during our stay and would seek out Brian's listings again.
Guest favorite

Guesthouse in Algoma

4.97 out of 5 average rating, 140 reviews

Country Farmhouse living

RaulRating, 5 stars4 days ago
We loved our stay here. Perfect, quiet, private area - very spacious. The yard had lots of seating, everything was labeled, and there was more than you will ever need for a 2 night stay. Will definitely be back!
Guest favorite

Guesthouse in Land O' Lakes

4.93 out of 5 average rating, 70 reviews

North Woods Pristine Lake Paradise!

LanceRating, 5 stars2 weeks ago
Wounded spot for a central base to explore surrounding areas very beautiful and peaceful
Guest favorite

Guesthouse in Hixton

4.96 out of 5 average rating, 113 reviews

Country Retreat. Beautiful sunsets and sunrises.

AmyRating, 5 stars1 month ago
Beautiful location, all the necessities and comforts of home. Well kept and spacious. Perfect for our daughter, husband, and I! Thank you for sharing your space!
Guest favorite

Guesthouse in Cornucopia

4.9 out of 5 average rating, 287 reviews

Waterfront Lake Superior's South Shore, "Sky Fire"

DawnRating, 5 stars1 week ago
We loved Eli's place. It was lovely, clean, comfortable and had everything we needed. We felt right at home immediately. The location is fantastic with beautiful views of the lake and a quiet, peaceful setting. Eli was proactive with his communication, friendly, and everything was so clear and easy that I didn't even have to contact him with any questions. Would definitely stay again and recommend it to anyone.

Destinations to explore