Vacation rentals in Sheboygan

Really good communication. The property owner was awesome & let us know not to leave a car on the street while a snow & ice storm hits rolled in. Then we went to leave at 6:30 AM, and the finishing touches were being completed to snow blowing the driveway. Great experience & cool place.

We had a great stay! Check in and out were simple, the home was immaculate, and the hosts are very responsive. We look forward to staying again!

Great location - felt away from it all but literally a couple minutes from the village. Cute digs that were immaculate and incredibly comfy beds. Hosts couldn’t have been nicer. Can’t wait to come back.

Felt like we were staying at a family members home. Very cozy and peaceful setting. We brought our dogs and they loved the large and fenced backyard. Plenty of space in the large bedrooms and living room. Kitchen had everything you could possibly need to cook anything you wanted. Host provided thoughtful treats for the dogs, and beverages and coffee. Even had prepared ice balls for beverages that was a nice touch. We loved our stay, worked great for our needs and would return again in the future if needed.

We had an amazing stay!!! Ellen was extremely friendly, welcoming and made you feel right at home. The place was in spotless condition and it’s very apparent the owner takes top notch care of the unit! The unit was actually much larger and spacious compared to what I was expecting. Everything you need for a comfortable stay.. and more! You will not be disappointed with anything in this rental, that’s a guarantee!! Thank you, Ellen!

I can’t gush enough about this place! I wish I would have stayed longer, and hope to return with my family later this summer. The yard is huge! Both local recommended restaurants I tried were fantastic. The shopping near by is plentiful, and the lake isn’t far away either although that’s not why I came. I just wanted to get out of Chicago for some peace and quiet. As a city girl, I ran into a little more wildlife than I was used to, but Jordan and his brother were super fast to respond, and quick to help me manage it! Throughout your stay, you can tell Jordan truly encourages traveling with your dog(s), and that kind of warm welcome is priceless.

We loved Mike & Laurie’s house! Our family (including our dog) spent a few wonderful days here. The house is super cute, the decorations and little touches are so great! The house has an awesome boho beach vibe, and it’s super cute and cozy. Great bedding, super comfy beds, you feel very at home and at ease here. Location is close to everything. Laurie was very responsive and proactive, check in and check out process was a breeze! We appreciated the book with suggestions on what to do in the area (don’t miss Faye’s Pizza and Field to Fork!). This house had everything we needed for a super easy stay. We will definitely be back!

I was traveling for work and planned to stay for one night but I loved the location, comfort of it that I stayed 2 nights!

Everything was perfectly in order, clean, stocked up on anything you may need. :)

This place offers the right balance between peaceful and relaxing while being close to everything. The house was clean and had all the essentials. We woke up every morning to amazing views . We went for 4th of July week and had the best view for fireworks without dealing with crowds. Everyone is friendly in the neighborhood. I had to work remotely for a few days and the sun room was perfect. You can’t beat working with those views. We will be back.

This place was perfect. If you're headed to Road America, the location could not be better. The home is right in between the race track and Elkhart Lake. We watched deer from the front window. This home was very comfortable and clean, I would definitely stay here 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!

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.

This place is suitable for a small family or a few adults. Very clean and well thought-out amenities made it quite attractive. Because we were very busy at Road America every day, we did not have an opportunity to use the kitchen except to make coffee, but had we wanted to cook, I'm sure we would have found everything needed. The only "warning" is that anyone with some mobility issues might find the stairway to the second floor a bit daunting. If we need a place in the area again, we would likely choose this house again.

We have stayed with Ryan several times because of the great location, excellent communication, and the clean and comfortable accomodations. The space is exactly as pictured and has all the amenities you will need for a great vacation. Highly recommend!

We couldn’t have asked for a more accommodating, clean place! Everyone in the group commented that we found “the spot” if we ever revisit Elkhart Lake. The house was spacious, clean, and well stocked with everything we needed. Even a charcoal grill that was put to use. Thank you! Hopefully it will be available should our race group come up to Road America again.

Can’t say enough positive things! Perfect place for families - plenty of space, well stocked, even has all the kids toys and great amount of beds / bedroom space.

I’ve stayed here before and will continue to stay here. The hosts are incredible and make your stay feel like you were invited. House is ADORABLE and has everything you could need. Location is prime! Love love love The Nest!

Great view and confortable stay .

Place was great! Only comment I have is the beds were too soft (I need a firmer bed) :)

We had an incredible stay at SurfDaze! The pictures don’t do it justice—this is a truly stunning beachfront property on Lake Michigan. The home was spotless, beautifully maintained, and exceptionally comfortable. Waking up to the sound of the waves and enjoying the breathtaking views made our trip unforgettable. We can’t wait to come back!

Excellent place, I was there for almost 2 months and is very peaceful, the place is exactly like photos, everything was great, Thank you Chris

Dustin was a welcoming, kind host. He gave us the option of letting ourselves in or ringing the doorbell to meet him. We decided to meet him and had great conversation. We loved that he took the time to get to know us, even though he has a busy family. If we didn’t want to, we easily could have just walked up the stairs to the apartment with no contact, but meeting him made it more personal and memorable. Other notes: Dustin was very responsive and proactive. Prior to arrival, he messaged us, warning that there’s a dog (Stella) who would probably bark at us upon arrival. Indeed, she was there but was as sweet as can be and loved alllll the belly rubs. We had a busy weekend in the area, but we took a little time to explore the beautiful property. The apartment was just perfect and the best thing was that we didn’t have to do anything for checkout, except pack up our own things. We hope to visit again when we are up in that area in the future. Thank you, Dustin!

We had a great time at this place. Everything was as described. Very easy to work with and accommodating.