Kid-friendly vacation rentals in Sheboygan County

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!

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!

Beautiful, well-appointed home with a heck of a view AND walking distance to downtown. Tricia was communicative and kind. Great experience!

This was an amazing property! Exceptionally clean, updated with great decor. Chris reached out with property details well in advance, and followed up to ensure we had everything we needed. They gave lots of great suggestions of local restaurants and attractions. The garage game room with the simulator was by far our favorite. We got a day in at Road America and two rounds of golf all from the comfort of this place. Highly recommend, we will be back. Thanks Chris!!

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.

We stayed for a week and felt right at home! It was spacious, well maintained and decorated, and had more than we needed. We especially loved the fenced in yard with decorative pond and the game room downstairs. We would definitely stay here again.

This is my favorite place to stay in the area. The property is beautiful and it is so quiet. We enjoyed a bonfire!

The host was very nice and a nice place to stay. Very clean and very close to the beach

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!!!

I have stayed here. few times always, easy and great to deal with will stay again in future!!! ⭐⭐⭐⭐⭐

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.

Eric’s place was wonderful! The location was fantastic. Walking distance to downtown, and close to the water. Though we were arriving late, Eric reached out to let us know we could come in early. His communication was excellent prior, during, and after our stay. I would definitely stay here again!

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!

The only place we stay when we're in town! Great to be back in our little home away from home.

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.

Sarah was always responsive to our questions and requests. The place was charming, and we really enjoyed our stay.

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

This place was incredible! So close to the river walk and beach and in the perfect location for restaurants and only a 20 minute drive to Road America! Will definitely stay again!

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.

Throughly enjoyed our stay. Close to the track. Loved the decor. Very clean. Hoping to stay there next year. Thank you Colleen

We enjoyed our week-long stay very much. Written instructions were concise and very clear. The neighborhood was calm and pleasant. We could view Lake Michigan from inside as well as the front and back porches. The condo felt larger than the actual square footage - mostly due to great organization and lack of clutter. The kitchen was wonderful for cooking. Thanks!

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