Holiday rentals with a fire pit in Sheboygan County

Flew in for business with Acuity Insurance. Perfect place to stay. Drove up to Green Bay for the Texans vs. Packers game. Only an hour drive from the house in Sheboygan. I will definitely stay here again when I come back to town!

We loved our stay at Curtiss Castle! This home is beautiful, clean, spacious, and just like the pictures. The neighborhood is quiet and peaceful…perfect for our winter getaway! We had no issues with our stay. Angelia was a great host and we would recommend this place to anyone!

This is our second time staying at Eric and Anna's place. They are perfect hosts! Their place is perfect, clean, roomy and just a stones throw from downtown Plymouth and Road America. We will be booking again! Thank you so much!

Now that I have stayed at Jack's home @ 5 times, I can easily verify that every moment spent in that home is magical - steps away from a walk on the beach, the methodical waves lapping on the shoreline, and the majestic sunrises reflecting on the water combine to provide a therapeutic sensory experience that delivers 24 hours each day. If that isn't enough, there are fabulous coffee shops, restaurants, and bars that you can walk to as well as many others a short drive away. No - Jack does not pay me to write these reviews ... the reviews write themselves. Enjoy!

We had a great stay at The Orchard House Retreat. The property is as described, looks like the pictures and had everything we needed. The kids especially loved all the toys and books! The house is 5 min to the State Park beach and 10 min from downtown. We loved having the backyard, the furniture was well taken care of and the fire pit was perfect for s’mores. The hosts were very responsive and accommodating— with everything labeled around the home. It’s also a great layout for bigger families /groups with 2 bedrooms upstairs, 1 on the main floor and 1 in the basement.

I would highly recommend Fairway Getaway to any folks looking for a fantastic stay in Wisconsin. Our group was traveling from out of state and it was so easy to stay here. Shawn is a great host, with a great place to stay at. The place is very spacious and clean! The golf simulator and proximity to plenty of restaurants and shopping makes this stay a 10/10.

We had a great stay. Home had tons a natural light, host was responsive and easy access to beach just steps outside the door.

Diana was super responsive and accommodated us quickly after plans changed. Her space is beautiful and clean - the kitchen is especially wonderful and would be great for a family trip. It's close to the beach and restaurants as well!

We stayed with our eldest son and youngest grandson to attend the vintage race weekend at RA. VERY close to restaurants in Elkhart Lake and also the track. Beds were fantastic and the home is spacious. Our grandson enjoyed the swingset playground too. We ended up cooking two meals using the gas grill and deck and the kitchen was well equipped. Our grandson didn’t want to leave. Four “real” bedrooms and we will be back with more people next year. We had few questions but they were answered immediately. If you are planning to attend an RA event I highly recommend staying here. If you plan to attend the Brian Redmond vintage event next year you will be competing with us hahaha.

What a gem! I truly think this property is highly undervalued. The grounds alone are magnificent. Such a gorgeous historic home and peaceful neighborhood. It felt private and secluded yet close to everything that we needed to get to and very walkable safe area. I cannot say enough good things about this Airbnb and hope to stay there again on future trips! Thank you to our wonderful Host, Julie, who was responsive, kind, and very accommodating of us.

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!

Perfect place for a quick trip to Sheboygan. Would for sure stay here again if we were back in the area! All the details were clearly communicated and even gave some great advice on places in the area to dine out.

We stayed at Chris’s place to visit nearby family with our two children and dog. The apartment was perfect for us: comfy beds and sofas; well-stocked kitchen; loads of games and books for entertainment. Lake Michigan is blocks away, and we took several (longish) walks to the beach and downtown shopping. Chris was quick to return texts, and he was a great host. 10/10 would return!

Fantastic stay on beautiful property. Very clean with EXCELLENT communication. Our first time in the area, we really appreciated all the help and the dining suggestions. Highly recommended.

This place was absolutely perfect and I will definitely stay again when back in Sheboygan. It’s a short walk to Lake Michigan and perfect for a nice evening stroll to downtown for dinner. Great place and just what I needed!

Our groups have been staying at Jennie's place for the last several years and always look forward to returning. The house is great for groups - lots of living and sleeping space for everyone. The set up is super fun with different floors and spaces to enjoy. The backyard is great for having a bbq or a campfire right on the lake. The area is nice and quiet as well as beautiful. Our groups are always impressed as soon as we pull up! The hosts are always available to answer quesitons and offer information and they always respond to emails/text super fast. We will definitely keep booking here!

We had a great stay! We were in for a race event at Road America. It’s about as close to the track as we could hope for, the cabin was clean and location in front of the lake was serene. Would stay again and would definitely recommend!

The first words out of our 19 year old’s mouth was, “Mom, this is the best one we have ever stayed in!” Everyone loved how cozy the place felt and how you could set the temp for each room, just the way you liked it, including in the bathroom if the morning was a bit chilly. The rustic charm is just beyond beautiful. I loved the swing set and sitting area around back. Our dog loved it. Overall, just an absolutely gorgeous place to be for an entire week. The beds were clean and comfortable. I would highly recommend to anyone looking for a nice get away.

We loved our stay in Cascade! The house was beautiful and the outdoor area was so peaceful and relaxing. Carla provided helpful and clear information, and she made our stay comfortable with thoughtful extra touches. It was the perfect spot for our family vacation!

We had a wonderful stay at Tim’s Airbnb! We booked it for my bachelorette party and the whole weekend was exactly what I was looking for. It’s in a gated community and all the way at the end of the road. It was so peaceful. The cabin has a nice living room area perfect for board games, a huge kitchen table where everyone fit to eat together and lots and lots of water toys. We were all able to go out and kayak / paddle board around the lake and end the night with a bonfire right along the lakeside. This Airbnb had everything we need to enjoy a peaceful fun weekend. When we realized we didn’t have any coffee the host ran right over with some to share. And our last morning even surprised us with a bundle of delicious homemade blueberry muffins. The windows and pantry area were a bit dusty but everything else was clean! We had the perfect weekend and would love to come back here again!

Title: A Perfect Getaway in the Woods 🌲✨ We had an incredible stay at this beautiful cabin in the woods. From the moment we arrived, we were impressed by how thoughtfully everything was prepared. The cabin itself was even more stunning than the pictures—immaculately clean, beautifully decorated, and full of cozy touches that made it feel like home. The surroundings were peaceful and private, with nature all around. We especially loved winding down by the fire in the evening. It truly felt like a retreat from everyday life. The host was responsive, kind, and made sure we had everything we needed for a comfortable stay. If you’re looking for a serene and charming place to unwind, this cabin is it. We’re already thinking about our next visit!

The accommodations were perfect for our short stay and Meghan was very responsive and helpful with our needs. We would love to visit again when we have more time to use all of the outdoor amenities.

Peaceful Retreat in the Perfect Location We absolutely loved our stay! The location was ideal—just a short walk from the lake and tucked in a peaceful, quiet setting that was exactly what we needed to unplug and relax. The home itself was spacious, beautifully decorated, and equipped with everything we needed for a comfortable stay. We spent time exploring the charming downtown shops and discovered a fantastic wine and cheese store. One of our favorite moments was sitting outside, sipping wine, enjoying our cheese, and finishing off the evening with a trip to a great little ice cream shop nearby. We also treated ourselves to massages at the Osthoff, which made the weekend even more rejuvenating. This place truly offered the perfect blend of calm and convenience. Dan was incredibly responsive and helpful throughout the entire stay. We would absolutely come back—highly recommend for anyone looking for some chill time. We would come back for Road America as well, they just were not racing