Holiday rentals with a fire pit in Sheboygan

We loved the house and accommodations. Host was extremely helpful and very quick to respond to any questions. Great location and spacious. Highly recommend.

I can't say enough about this beautiful lake house! Greta is one of the finest hosts that I've ever come across. Timely information, quick responses, and there are so many extras!! So many toiletries, pantry, and fridge items for your comfort and convenience. We visited in October, so didn't need them, but a caddy by the rear door with suntan lotion and beach towels. Just an extremely considerate person. We enjoyed our stay very much and would love to return in the future.

Our family has stayed in several rental homes and this property definitely stood out as one of the best we have ever stayed at. The house was very clean. The owners have thought of everything. Lots of games and fun things for the kids to do, extra toiletries ,( toothpaste, toothbrushes, shaving cream, razors and soap and shampoo in every bathroom. Local samples of food n the fridge, beer, wine, pop, cheese, and coffee. We would definitely stay their again.

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!

Absolutely loved the boat house and amazed by how much thought was put into all accommodations on the property

The place was clean, nice and good amenities. Mary was responsive to our questions and very helpful. We were there for the SCCA Championship races at Road America ! We Left at 7am and returned at 10pm everyday. We did enjoy it. We only wish the upstairs bathroom had a shower instead of a soaking tub. (Since 4 guys all trying to take a shower before rushing off to sleep. Very nice place.

Two moms an infant and two adolescent children stayed for a quick weekend exploring Cheboygan and this place was perfect, Ryan our host was extremely responsive and helpful and everything was exactly as it was described. We are very happy with this stay.

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.

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.

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!

I’ve stayed here twice now and both times have been wonderful. The place is on the second floor, with the sweet owners below, and it is just the coziest space! My favorite thing to do is eat breakfast by the window with beautiful greenery and birds outside. Honorable mention goes to the bathtub! Many a sore muscle has been soothed after a long hike on the Ice Age Trail down the road. Carrie is awesome. She is super helpful and very quick to respond - it made me feel safe knowing they were just downstairs. Highly recommend this place!

Connie and rich were amazing host . They showed love and kindness to us . If I need a place in kewaskum again i definitely would rent the place out again . Very beautiful place !

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.

A beautiful cabin inside and out. We had a great time inside and outside the cabin. Enjoying the fire and smores, the records and DVDs, and kayaks and on the lake. Pictures don't do it justice. Would love to come back one day!

This couple was amazing! So responsive, so willing to give us the best time away and to fully enjoy the little time we had! We were only able to go one night but it truly felt like 3. We are going back to work feeling reset and relaxed. Cannot wait to come back

Great place, great location, and no doubt our go to place when in town working. I highly recommend!

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.

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!

This was our second time staying here and we loved it just as much as the first! It’s the perfect place to unplug in the country for a few days. The kitchen is great for cooking, the beds are very cozy, and the shower is wonderful. Our favorite part is plugging in our laptop to watch movies on the projector in the evening. Rachel and David are awesome hosts and very communicative if you need anything. Thanks for a great stay!

We had an amazing stay at Pine Dunes Cabin! The home was even better than expected—spacious yet cozy, with a beautiful rustic-modern vibe. The beds were incredibly comfortable, and there was plenty of space for our group of six to relax and enjoy. The setting is peaceful and private, just a short walk from the beach, and the decks and fire pit made for perfect evenings. One afternoon, our group walked to the beach for a cold plunge in Lake Michigan and enjoyed the hot tub afterward. The kitchen was fully stocked (we cooked several meals), and every detail felt thoughtfully considered. Jeremy was fantastic—super communicative and helpful from start to finish. We loved our stay so much we wanted to add another day, but (not surprisingly) it was fully booked! If you're looking for a peaceful and rustic yet luxurious getaway, I would highly recommend Pine Dunes. We’ll definitely look to stay again when we’re in the area.