Guesthouse vacation rentals in Wisconsin

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Wisconsin guesthouse rentals

Family-friendly guest house rentals

Top guest favorite
Guesthouse in Richfield
4.94 out of 5 average rating, 257 reviews

Peaceful weekend or extended stay, full amenities

LauraRating, 5 stars4 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 favorite
Guesthouse in Cashton
4.97 out of 5 average rating, 338 reviews

Enjoy your space at the Mielke Way!

NicholasRating, 5 stars4 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 favorite
Guesthouse in Stoughton
4.94 out of 5 average rating, 374 reviews

Country cabin, birders paradise.

PaulRating, 5 stars3 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 favorite
Guesthouse in Hudson
4.96 out of 5 average rating, 185 reviews

Cottage in historic Hudson, 5 blocks from DT

SarahRating, 5 stars1 week 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 favorite
Guesthouse in Madison
4.98 out of 5 average rating, 312 reviews

Boutique Eco Hideaway - Willy Street

CarolineRating, 5 stars7 months ago
This has to be one of my favourite AirBnBs I have stayed in across the USA and Europe. Jackie’s place was perfectly located, close to the lake and 2 minutes walk from Willy St for shops and restaurants. A very private setting in the backyard of their main house, with off road parking. Everything was beautiful, with high end furnishings, crockery, bedding etc., and an especially comfortable bed and sofa bed. And such a thoughtful welcome gift of local cheeses, crackers, chocolates, nuts, fruit and beer!Yes there are cheaper places in Madison, but this is perfect proof that you get what you pay for and it was worth every penny. Thank you Jackie for making mine and my Mum’s stay in Madison so comfortable! We hope to be able to return one day!
Guest favorite
Guesthouse in Spring Green
4.95 out of 5 average rating, 116 reviews

Teacher’s Lounge

KimRating, 5 stars1 week 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 favorite
Guesthouse in Earl
4.99 out of 5 average rating, 167 reviews

Earl Eddy

MagdalenaRating, 5 stars1 day ago
Beautiful place surrounded by woods. The apartment looks brand new! I have previously stayed in the hotels in the area and this place is much better value. Will definitely consider coming back and share the location with friends!
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.

Guest house rentals with a patio

Top guest favorite
Guesthouse in Stratford
5 out of 5 average rating, 31 reviews

Cozy Cabin | Pond View | Rock Ridge Orchard & Lake

CindyRating, 5 stars2 days ago
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!!
Guest favorite
Guesthouse in Sturgeon Bay
4.96 out of 5 average rating, 69 reviews

Cozy 1 bedroom guesthouse with fireplace

IsabellaRating, 5 stars2 weeks 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 favorite
Guesthouse in Ashland
4.88 out of 5 average rating, 48 reviews

Beach Front Hideaway

RaeAnnRating, 5 stars2 days ago
Our recent trip to this charming Airbnb was nothing short of magical. From the moment we arrived, we were captivated by the breathtaking views of Lake Superior right outside the door. The property is beautifully located, offering both privacy and easy access to the sandy shoreline. The space itself was cozy, clean, and thoughtfully decorated. We especially loved waking up to the sunrise over the lake and enjoying evenings on the deck. Communication with our host was seamless; they provided helpful local tips and made us feel welcome from start to finish. If you're looking for a peaceful retreat with stunning natural beauty, I highly recommend this Airbnb. We’ll definitely be returning!!
Top guest favorite
Guesthouse in Waupaca
5 out of 5 average rating, 22 reviews

Silver Lake Studio

KateRating, 5 stars1 day ago
Mark and Mary Fran's guest house is extremely clean and well appointed. It was a beautiful and peaceful location for a nice get away. We loved sitting on the porch and listening to the birds. I would definitely recommend the guest house to anyone looking for a quiet place to relax.
Guest favorite
Guesthouse in La Crosse
4.94 out of 5 average rating, 83 reviews

Mississippi River - cozy 1 bedroom

MargaretRating, 5 stars6 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 favorite
Guesthouse in Maiden Rock
4.97 out of 5 average rating, 33 reviews

Cozy Guest House Getaway

KarinRating, 5 stars4 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 favorite
Guesthouse in Horicon
5 out of 5 average rating, 18 reviews

Boathouse Bungalow

HeidiRating, 5 stars4 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 favorite
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 washer and dryer

Top guest favorite
Guesthouse in West Bend
5 out of 5 average rating, 83 reviews

Wilderness Retreat*Private Deck*Gazebo*Fireplace

JonathanRating, 5 stars3 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 favorite
Guesthouse in Egg Harbor
4.98 out of 5 average rating, 51 reviews

Village Tree House, chill setting walkable to town

AllisonRating, 5 stars2 weeks 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 favorite
Guesthouse in Somerset
5 out of 5 average rating, 25 reviews

Somerset “Casita”in the Pines & Peacocks

LisaRating, 5 stars4 days ago
Beautiful casita and beautiful property. Loved having a dog door to an outdoor fenced kennel for the pups and access to laundry. The walking trails and getting to see the peacocks were a great bonus. Clean, organized, comfortable, and cute. Perfect landing spot while visiting the area and would love to stay again.
Top guest favorite
Guesthouse in Ladysmith
4.98 out of 5 average rating, 53 reviews

The Bunkhouse, a Northwoods Escape

SusanRating, 5 stars2 weeks 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 favorite
Guesthouse in Emerald
5 out of 5 average rating, 23 reviews

Emerald Acres Retreat

EricRating, 5 stars3 days 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 favorite
Guesthouse in Baileys Harbor
4.95 out of 5 average rating, 59 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 favorite
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 favorite
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