Kid-friendly holiday rentals in Sheboygan County

For a quick weekend getaway and change of scenery, Dan’s place was perfect. Easy to get to, and near restaurants and downtown area. Whole house makes it feel homey and comfortable. Would definitely stay again, and recommend!

Thank you Todd for a wonderful stay! Our group really enjoyed the property and selection of board games to play! Very convenient location to local spots and restaurants. Very simple and direct check in/out progress and great communication. Would love to stay here again if I’m ever in the area!

This is the second time I stayed at Chelsea’s house. It is the perfect location for the beach, the river and the downtown Sheboygan area and also super close to Kohler for the spa and food and wine festival! Perfect cozy home for a girls trip or a family get away!

Charming country home which was a great place for us to relax after attending the races at Road America all day. Very clean and had everything we needed.

I'm not sure what I can add to all the other reviewers opinions. This is a great Airbnb and we've stayed in over 170. The hosts really put a lot of thought into making it perfect for guests. We came here to look for some special birds. Jaclyn's home is a birders paradise with six feeders in a wonderful backyard. If you look on a map, the home looks near the highway, but road sound is very minimal. The attached townhouse also did not create any audible sound. Please be respectful of them too.

We stayed here for a golf trip and could not have been more pleased! We've stayed in a lot of places, but this one was the best, by far!!! Alyssa was always quick to answer any question I had and made sure we had everything we needed. We had plenty of room and I only wish we had more time there. Thank you!!

Loved this house for a girls trip! Backyard and fire pit was perfect, everyone got their own room, and the kitchen had everything we needed to cook at home.

Michelle and John saved our girls trip. After another site's rental was cancelled on us literally while we were driving to it, we found this place. They responded so quickly and were able to accommodate us last minute. The house and property was beautiful! We had plenty of room for all of us, and the kitchen was the perfect spot for our extensive snacking. We really enjoyed sitting in the yellow chairs and enjoying the view of the lake. We had everything we needed and then some. I can't recommend this property enough!

My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!

We enjoyed our stay. It was clean just like the photos.

Missy and Kyle's apartment in Sheboygan was truly a great recombobulation station! The location was spectacular with only two blocks to Lake Michigan in one direction and two blocks to great dining, farmers market, coffee shops, and local shopping in the other direction. The apartment was incredibly clean, cozy, and comfortable for some rest and relaxation in-between our local adventures. It was a lovely home away from home with everything you would need to prepare meals. And in the event you've forgotten something at home, there is a good chance Missy has thought about it for you.

Our stay in Sheboygan was just what we hoped for! We stayed busy doing a variety of things each day and night during our weekend getaway. It was wonderful coming back to a space that was cozy and clean. Geoff provided a very helpful guidebook and gave us additional recommendations when we asked. Thanks Geoff!

This is such a gem! We traveled with 2 young children and after a day at Road America it was EVERYTHING we needed. We didn’t get a chance to try to sauna or cold plunge, but the place felt just like home and was so convenient. We can wait to visit again!

Chris was a great host! Our other Airbnb didn’t respond to us and he was able to get us in with a same day reservation! He was very friendly, brought us a high chair and provided some local snacks for our stay! The house was spotless and the backyard and neighborhood were so cute! We will be staying with you again next time we’re in Sheboygan!

the place was great and we were so happy to be able to bring our dog with us. I was pleasantly surprised to see no dog hair from previous renters. very clean. Ashton and James were great! they were quick with all requests and super friendly. we had an emergency when we got back from our stay because my daughter left her koala lovey at the Airbnb. 😊 Ashton and James were prompt in their response and mailed the lovey to us. thank you!

Thank you for hosting us. It was exactly what we needed to rest and be ready to go to our daughter’s baby shower the next day.

Brian’s instructions to check in was very good. The condo was very clean and the views were great. Short walks to great restaurants and the beach. Every night we ended our day sitting on the patio looking out at the lake. Definitely a place I’d rent again when I visit Sheboygan.

The accommodations were perfect for a large gathering. Lots to see and do just within walking distance. Beautiful location and the space was perfect for our family gathering. Great home with all you needs. Lovely bedrooms with very comfortable beds. Great time was had here Sally

Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.

We absolutely loved our location so close to the beach and harbor area! We had everything needed for our stay. There is the perfect little ice cream shop a block away! Parking on the street available right in front of where we stayed. There is a book in the apartment with comments from previous guests with notes on great things they discovered while there as well. We contributed before our departure. We would absolutely consider another stay in the future if we visited again. Sheboygin is a beautiful place. Park across the street made it so easy to see out and over the harbor providing a great view allowing for a great walk to see things. Definitely a "10" in our books!

Janelle’s place was spacious and sparkling clean. The location is great, right on the river and an easy walk to the lake. We would definitely stay again if we come back to Sheboygan.

Very cool and well themed condo situated right between downtown Elkhart Lake and Road America. Was perfect for our group of 4. We would definitely recommend!

Beautiful location. Everything was great from the beginning to the end of our stay. We can’t wait to go back for another stay.

Had a wonderful stay. The location was perfect for us. Loved the restaurants that we could walk to.