Guesthouse holiday rentals in Wisconsin

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Wisconsin guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Richfield
4.94 out of 5 average rating, 257 reviews

Peaceful weekend or extended stay, full amenities

LauraRating, 5 stars3 weeks ago
Cute stay! We had a wedding at Homestead Hollow and this place was perfect! Cute and fresh baked cookies on arrival. Entrance is on the backside of the house, but the host was super helpful on finding it. Plenty of room to spread out. Also exactly as described. It is a working farm with the family living there, but the space is as described. Although, it’s in the country - it’s also fairly close to lots of shopping, restaurants and parks.
Top Guest favourite
Guesthouse in Cashton
4.97 out of 5 average rating, 338 reviews

Enjoy your space at the Mielke Way!

NicholasRating, 5 stars3 weeks ago
Our stay at Allen’s place was perfect. They had fresh fruit, bread and other goodies for us at the home. The land was beautiful and very peaceful. We will most definitely stay again if we find ourselves in the area.
Guest favourite
Guesthouse in Stoughton
4.94 out of 5 average rating, 374 reviews

Country cabin, birders paradise.

PaulRating, 5 stars2 weeks ago
If you like a peaceful country setting with beautiful walking areas (among occasional passing goats too!) and a cozy woods cabin, this is the place for you. Only minutes from downtown Stoughton, warm generous hosts, and friendly neighbors.
Guest favourite
Guesthouse in Hudson
4.96 out of 5 average rating, 185 reviews

Cottage in historic Hudson, 5 blocks from DT

SarahRating, 5 stars6 days ago
We enjoyed The Cottage very much. It was a great getaway weekend for our 30th anniversary. We appreciated the Black Rooster Bistro recommendation! Best meal we have had eating out in a while!!! We wish Kay all the best with the space. It’s so relaxing and cozy!
Guest favourite
Guesthouse in Spring Green
4.95 out of 5 average rating, 115 reviews

Teacher’s Lounge

KimRating, 5 stars6 days ago
LOVED this place!! The garden outside is spectacular. Daisy the dog is a sweet greeter, and Aaron was super friendly and helpful. We love the Spring Green area, and this location could not be more perfect. The space is spotless, comfy, quiet, and looks exactly like the pictures. We will be back the next time we come to see a show at APT!! Thank you for your kind hospitality.
Top Guest favourite
Guesthouse in Maiden Rock
4.97 out of 5 average rating, 33 reviews

Cozy Guest House Getaway

KarinRating, 5 stars2 days ago
It really worked well for us to use this cottage as a home base for exploring this beautiful area! Would suggest letting people know that many businesses are closed M-W - we love the Stockholm Pie and General Store which was open and excellent :)
Top Guest favourite
Guesthouse in Earl
4.99 out of 5 average rating, 166 reviews

Earl Eddy

LisaRating, 5 stars3 weeks ago
We needed to be near Trego and I was so happy to find such a cute place so close. The Eddy was full of thoughtful touches and you can tell the hosts take pride in it. We would definitely stay again.
Superhost
Guesthouse in Green Bay
4.73 out of 5 average rating, 180 reviews

Guest house near Lambeau field

DanRating, 5 stars1 month ago
Great place to stay for the NFL Draft. Easy Uber access, but far enough away to escape the intensity of the event as needed. Daniel was a great host, keeping me informed right up to check-in. Will definitely consider renting again when I’m in Green Bay again.

Guesthouses with a patio

Top Guest favourite
Guesthouse in Stratford
5 out of 5 average rating, 31 reviews

Cozy Cabin | Pond View | Rock Ridge Orchard & Lake

CindyRating, 5 starstoday
Shelly‘s place was very beautiful and they thought of everything that one could possibly need to have a pleasant stay!! The outdoor landscaping and pond was amazing. There was so much to do and such a cute place. I would definitely go back again and highly recommend it!!
Superhost
Guesthouse in Birchwood
4.67 out of 5 average rating, 3 reviews

Northwoods Antler Lodge

SheilaRating, 5 stars3 weeks ago
Had a wonderful time, Melissa answered our questions and was very helpful and responded in a timely manner House is secluded and enjoyed the deer and elk, spent 4 days in our side by sides with 3 other couples, area is very beautiful, would stay here again Guest house was clean and loved the outdoor theme of the decor.
Guest favourite
Guesthouse in Sturgeon Bay
4.96 out of 5 average rating, 69 reviews

Cozy 1 bedroom guesthouse with fireplace

IsabellaRating, 5 stars1 week ago
Great place in an awesome location. Easy to get to downtown and lots of hiking spots. Place was spotless and had everything we might need. We brought our pups and there was a nice backyard for them to use and the house was super accommodating. Perfect for our weekend getaway!!
Guest favourite
Guesthouse in Ashland
4.87 out of 5 average rating, 47 reviews

Beach Front Hideaway

NancyRating, 5 stars6 days ago
Very peaceful spot with just enough room. Private and beautiful beach. Decks were wonderful for lounging with a cup of coffee (or wine) listening to the waves. A nice place to come back to after a day of adventuring.
Top Guest favourite
Guesthouse in Waupaca
5 out of 5 average rating, 21 reviews

Silver Lake Studio

LucyRating, 5 stars1 week ago
Beautiful & dainty place for two. Kitchen and bathroom full of items one would need. We did not do much exploring as we really wanted to relax and do nothing, but the information binder was full of recommendations in the area. The deck was great to go and sit out on to enjoy the weather and scenery. Would recommend to others!
Guest favourite
Guesthouse in La Crosse
4.94 out of 5 average rating, 83 reviews

Mississippi River - cozy 1 bedroom

MargaretRating, 5 stars4 days ago
We absolutely loved this little cabin. It was clean and had everything we needed. The bed was extremely comfortable too. The fishing was great. My son caught some of the biggest fish I’ve ever seen. I highly recommend it. It’s great for a couples get away or a small family vacation. The yard is big enough for kids to play in and it’s in a safe neighborhood. It was just perfect. We’re definitely going back.
Top Guest favourite
Guesthouse in Horicon
5 out of 5 average rating, 18 reviews

Boathouse Bungalow

HeidiRating, 5 stars2 days ago
Mary’s cottage is a gem!! It was spotless, well designed, and had everything I needed. The cottage is right on the shore with gorgeous views of the river. I stayed here to visit Horicon Marsh but would have liked another day or two just to enjoy these views and watch the pelicans.
Top Guest favourite
Guesthouse in Gays Mills
5 out of 5 average rating, 76 reviews

The Bunkhouse on 80 acres, trails

AshleyRating, 5 stars1 month ago
What an amazing stay! My partner and I (and our dog!) will definitely be back. The space was so cozy and simple, the beds were really comfy, the wood burning stove was amazing, and the surroundings were so beautiful. We saw so many birds and took some amazing walks, but mostly just relaxed and enjoyed the weekend. Can't wait to return during all the different seasons! Kevin was a great host, too.

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in West Bend
5 out of 5 average rating, 83 reviews

Wilderness Retreat*Private Deck*Gazebo*Fireplace

JonathanRating, 5 stars2 weeks ago
Our stay at Don and Betsy’s place was nothing short of exceptional.From the moment we arrived, we felt warmly welcomed and completely at home. The property was immaculate-and properly maintained, thoroughly decorated, and stocked with every comfort we could possibly need. Don and Betsy were the perfect hosts: friendly, responsive, and full of recommendations if needed. It’s clear they genuinely care about providing an amazing guest experience. The peaceful surroundings, cozy touches, and attention to detail made this one of the best Airbnb stays we ever had. If you’re looking for a quiet, comfortable, and memorable getaway in Wisconsin, look no further. We’re already planning our next trip!! Thank you again! Jonathan and Lisa
Guest favourite
Guesthouse in Egg Harbor
4.98 out of 5 average rating, 51 reviews

Village Tree House, chill setting walkable to town

AllisonRating, 5 stars1 week ago
This place was so cute and adorable. The furnishings and design were very well thought out and went together perfectly. It was very easy to find and get in with the automatic lock. It wasn’t super private being on the same lot of the main house and another cottage. We didn’t hear the neighbors or anything so it was still quiet. It had everything that was needed for two people. There just wasn’t a closet, and some hangers would’ve been nice to hang up clothes. Or an optional clothing rack. But would definitely recommend and stay here again. It was very close to shops, restaurants and winery’s.
Top Guest favourite
Guesthouse in Somerset
5 out of 5 average rating, 23 reviews

Somerset “Casita”in the Pines & Peacocks

AmandaRating, 5 stars2 weeks ago
We absolutely loved the all the intriguing and thoughtful details in this cozy and comfortable home. Surrounding area was peaceful and beautiful and it was a great location, not far from destinations but just far enough to have a quiet retreat that felt like home. Great value and Kelly was wonderfully inviting and communicative, while also respectful of privacy and space. Would love to stay again. 😊 thanks Kelly!
Top Guest favourite
Guesthouse in Ladysmith
4.98 out of 5 average rating, 53 reviews

The Bunkhouse, a Northwoods Escape

SusanRating, 5 stars1 week ago
My niece and her family stayed in the bunkhouse for a local family event and enjoyed their stay immensely. I communicated with Courtney about possible early check-in and the option to gather around the beautiful firepit in the evening with extended family, and Courtney was gracious to allow and responded quickly to our requests. I highly recommend the Bunkhouse for a quiet and peaceful get-away.
Top Guest favourite
Guesthouse in Emerald
5 out of 5 average rating, 23 reviews

Emerald Acres Retreat

EricRating, 5 stars1 day ago
Had a great time at this AB&B! Jim & Molly go above and beyond to make you feel welcome and the location is peaceful and private. Highly recommended 👍
Guest favourite
Guesthouse in Baileys Harbor
4.95 out of 5 average rating, 58 reviews

Lighthouse Lookout

GraceRating, 5 stars3 weeks ago
Kyles place was just perfect for what we needed! My husband and I really enjoyed our stay here during our small getaway in Door County. The bed was super comfy, the decor was cozy— overall, a really relaxing spot to unwind after a day of Door County activities.
Top Guest favourite
Guesthouse in Cable
4.95 out of 5 average rating, 129 reviews

The Nest at Drumming Woods

Laurie And AdamRating, 5 stars5 months ago
Janice’s place was warm and welcoming even on the coldest of weekends! We had everything we needed to make the most of our time in beautiful Cable. We will be back!
Guest favourite
Guesthouse in Land O' Lakes
4.93 out of 5 average rating, 70 reviews

North Woods Pristine Lake Paradise!

LanceRating, 5 stars8 months ago
Wounded spot for a central base to explore surrounding areas very beautiful and peaceful

Destinations to explore