Holiday rentals with outdoor seating in Sheboygan

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!

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!

Joe and Alyssa 's property was amazingly beautiful ! All my siblings us came from out of town and state , to see our baby brother walk for his high school graduation in Sheboygan . This home housed us all with the main house and guest house . Very fast communication with the owners and they were able to adjust our reservation so quick for us to book the guest house that last minute too . The grilling space was wonderful , as we had kids who ran around the yard - Safely without any concerns . Will definitely look forward to booking with Joe and Alyssa again in the future !

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.

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.

Our family really enjoyed the house and the amenities this house had to offer. It felt like a home and so inviting.

Very unique (in a good way!) property, thanks for making it available for us to use! Very easy to work with hosts and a meticulously maintained property. Highly recommended!

Great place and great hosts. They’re super responsive and helpful. The Coffee Corner next door is a must try and convenient.

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!

Doug was an excellent host making sure everything was perfect during my stay if im ever in Sheboygan again I’ll definitely be staying here 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!

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!

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 !

Beautiful condo. Would absolutely stay here again!

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

Beautiful condo with well stocked kitchen, very nice bathrooms and great walkable location!!

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.

Awesome place!

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.

We enjoyed our stay. She was very responsive and the location can't be located in a better spot. Will definitely stay again.

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