Guesthouse vacation rentals in Wisconsin

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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, 255 reviews

Peaceful weekend or extended stay, full amenities

BrianRating, 5 stars4 months ago
I had a great experience with Matt & Laura. They did a great job communicating and their property is very nice!
Guest favorite
Guesthouse in Milwaukee
4.95 out of 5 average rating, 258 reviews

The Carriage House in Sanger House Gardens

SamuelRating, 5 stars2 weeks ago
We enjoyed our stay and the gardens were beautiful. This was a great stay with great eateries within walking distance. Whenever we are back visiting Milwaukee we sure will look at booking to stay here again.
Guest favorite
Guesthouse in Hudson
4.96 out of 5 average rating, 184 reviews

Cottage in historic Hudson, 5 blocks from DT

AllisonRating, 5 stars4 days ago
Great place. Cozy & peaceful place to stay. Would stay here again.
Guest favorite
Guesthouse in Spring Green
4.95 out of 5 average rating, 113 reviews

Teacher’s Lounge

HollieRating, 5 stars1 week ago
Cute little spot. Great for weekends away. Downtown is walking distance and has a variety of shops. Cell service can be hit or miss, but not fault of host. Daisy is very sweet and will come greet you for pets. House was very comfortable and has everything you need (except washcloths, so if you're used to that bring your own). We enjoyed our time and would recommend it for anyone coming to the area.
Top guest favorite
Guesthouse in Maiden Rock
4.97 out of 5 average rating, 32 reviews

Cozy Guest House Getaway

AimeeRating, 5 stars1 month ago
I wanted a nice, quiet place to go with my dogs for a workcation. Danni's place was perfect for that! Pet-friendly, comfortable, and easy to access areas and activities. Though located next door to the owners, it felt private and secluded. Oh, and I loved the bed--slept so good! :) Thank you.
Top guest favorite
Guesthouse in Earl
4.99 out of 5 average rating, 165 reviews

Earl Eddy

KennethRating, 5 stars1 week ago
An amazing place and so well organized and easy to find. I was amazed at how beautiful and comfortable to stay here. Super quiet and serene yard and woods surrounding it. The host thought of everything and made it all easy for guests. You will not be disappointed at all with this place. Thanks again for making your beautiful place available!
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.
Superhost
Guesthouse in Pepin
4.83 out of 5 average rating, 6 reviews

Harbor Hill Inn - Carriage House

KarlynRating, 5 stars45 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

Top guest favorite
Guesthouse in Stratford
5 out of 5 average rating, 30 reviews

Cozy Cabin | Pond View | Rock Ridge Orchard & Lake

MichaelRating, 5 stars1 week ago
Shelly’s place was very clean and inviting. The property is beautiful. Shelly and Bob are both very friendly and welcoming. Great stay definitely recommended!
Guest favorite
Guesthouse in Ashland
4.89 out of 5 average rating, 45 reviews

Beach Front Hideaway

RileyRating, 5 stars1 month ago
Amazing location and friendly hosts. The best beachfront in the area. private location at the end of a private road. Beautiful BNB, nice architecture. Big kitchen and communal space.
Top guest favorite
Guesthouse in Waupaca
5 out of 5 average rating, 18 reviews

Silver Lake Studio

PamelaRating, 5 stars1 week ago
Mark and Mary's loft was the perfect weekend get away that we were looking for. The location is on a serene small fishing lake with beautiful views. It's close to the Chain 'O Lakes and Hartman Creek State park in the beautiful Wisconsin North woods. The loft is designed so nicely with a large deck overlooking the lake. We enjoyed eating meals out on the deck and watching the sun rise in the morning. The birds are just incredible to listen to at sunrise. The loft is tastefully decorated and well stocked with everything you would need in the kitchen and very comfortable. Extra blankets are provided for chilly nights. Mark and Mary were both such nice people and incredible hosts, quick to answer any questions and make local recommendations; we enjoyed getting to know them both and spent an evening by the fire pit with them. We would love to stay at their loft again in the future. It is just the location we were looking for and we are so happy we met them and found their gem!
Top guest favorite
Guesthouse in Emerald
5 out of 5 average rating, 19 reviews

Emerald Acres Retreat

ChrisRating, 5 stars3 weeks ago
The Retreat at Emerald was perfect for my friend, my dog, and me. The room was much larger than expected and had all the amenities we could wish for. The building and the grounds were very pet friendly, and my dog Hannah could not have been happier with her stay. Jim started a bonfire for us our first night, and all of the fixin's for s'mores were already inside. The trails in the woods behind the house were perfect for an afternoon walk. Would highly recommend this retreat for anyone looking to get away from it all.
Superhost
Guesthouse in Baileys Harbor
4.87 out of 5 average rating, 31 reviews

Jack's Little House

CathyRating, 5 stars7 months ago
Cozy & quaint! Quiet but close to all that Door County has to offer. It was clean and decorated so cute!
Guest favorite
Guesthouse in La Crosse
4.94 out of 5 average rating, 80 reviews

Mississippi River - cozy 1 bedroom

MeganRating, 5 stars1 week ago
This place was beyond perfect. I don’t want to post reviews to make other people rent it out, I want it all to myself. This cabin was the cutest! The views were incredible!! It was so peaceful, very clean, and all around great! I cannot wait to go back!
Superhost
Guesthouse in Lake Nebagamon
4.79 out of 5 average rating, 29 reviews

The Beach House on Lake Nebagamon.

RyanRating, 5 stars9 months ago
This small, converted beach house is perfect for two people. Nothing fancy, but everything you need. Lake Nebagamon is 20 feet from your bed. The dock and lake frontage is well kept and a good spot to wake up and walk around. David met us on arrival, showed us around - very welcoming. There is a tub inside the space, but the shower is enclosed and outside directly next to the beach house. Great stay, thank you!
Top guest favorite
Guesthouse in Manitowoc
5 out of 5 average rating, 27 reviews

Mallard Manor - Adorable 2 b/r guest house.

JoetteRating, 5 stars6 months ago
Mari was extremely accommodating with our very late check in over Thanksgiving! Everything was clean and tidy upon arrival and all basic amenities provided. This is a cute place in the country (but easy to find and not far off the main roads)! Would highly recommend and plan to stay again in the future when we come down for another Packers game! GO PACK GO! Thank you for sharing your space with us!

Guest house rentals with a washer and dryer

Top guest favorite
Guesthouse in West Bend
5 out of 5 average rating, 81 reviews

Wilderness Retreat*Private Deck*Gazebo*Fireplace

Gina MariaRating, 5 stars1 week ago
I don’t usually write reviews, but I felt compelled to share my experience because this place—and the people behind it—offered me something far deeper than just a stay. I came here in the midst of unimaginable grief, after losing my daughter. I needed a space that would allow me to breathe, cry, remember, and begin to gather the strength to carry on. This home was exactly that. Peaceful, quiet, and full of comforting details that made it feel like a gentle embrace rather than just a rental. From the moment I arrived, I could feel the care that had gone into preparing the space. It was spotless, beautifully arranged, and there was a calm energy. The natural surroundings added to the serenity—I found myself sitting in silence, listening to the wind or watching the light shift throughout the day, which became small, healing moments. The hosts were beyond accommodating. When I let them know why I chose their home, I was received with a warm embrace. If I could leave more words I would
Top guest favorite
Guesthouse in Sturgeon Bay
5 out of 5 average rating, 14 reviews

Spacious 2BR guest house with full kitchen

RebekahRating, 5 stars7 months ago
This was the nicest airb&b we have ever stayed in. So clean, comfortable and located conveniently to everything we needed. We have already recommended it to family planning a trip to Door County next spring. Loved it. Thank you.
Superhost
Guesthouse in De Pere
5 out of 5 average rating, 7 reviews

Guesthouse on the water 3.9 miles to Lambeau

PaulRating, 5 stars17 months ago
A great little house. would be perfect for a football party, but I stayed there for the holidays with my kids and it was great for us, too!
Top guest favorite
Guesthouse in Somerset
5 out of 5 average rating, 21 reviews

Somerset “Casita”in the Pines & Peacocks

AndreaRating, 5 stars1 day ago
The Casita is a wonderful, peaceful place to escape to. The unit is beautifully decorated with a Costa Rican vibe. It has everything you need for meal prep for a weekend or longer stay. Great outdoor seating areas, including the awesome firepit with lots of firewood too. We hope to return again. Thank you Kelly for being a great host.
Guest favorite
Guesthouse in Ojibwa
4.97 out of 5 average rating, 36 reviews

Club Suite Recreational Retreat

KathyRating, 5 stars2 weeks ago
We have stayed at this location before and always enjoy it! Will come again!
Top guest favorite
Guesthouse in Westby
5 out of 5 average rating, 45 reviews

The Honey Haven

JamesRating, 5 stars1 month ago
I didn't have the opportunity to meet Jennifer as we had a short stay, but every part of our stay was flawless. It is a drop-dead beautiful location and very peaceful. Fun little towns like Westby and Viroqua are only minutes away, and the gift honey was delicious! It is a very new, nicely decorated, and effectively laid out space that allows for big get-togethers and also private space. It is decorated very nicely, and everything works. Jennifer is extremely friendly, inviting, and super to work with - I will definitely be back and give her the highest recommendation! Thank you Jennifer! Jim
Guest favorite
Guesthouse in Baileys Harbor
4.95 out of 5 average rating, 57 reviews

Lighthouse Lookout

GraceRating, 5 stars2 days 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 stars4 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!

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