House vacation rentals in Sheboygan

This is a warm, inviting home with a terrific location in the lake. Jana and Josh’s house was very comfortable, clean, spacious and stocked with everything we needed for our vacation. An absolutely beautiful spot on the lake. Jana and Josh were extremely helpful and generous hosts who really anticipate what guests may need. We loved our stay!

Spacious home that accommodates so many people. The hot tub was lovely. You can fit a whole bunch of people in there and nobody's toes are touching.

Great stay! My group loved it and had a blast. House was Beautiful & Host was GREAT, was very understanding and helpful. DEFINITELY recommend and would love another stay sometime.

Had an amazing weekend here for a fishing trip/birthday weekend with a group of guys! Plenty of stuff to do on the property, pretty much took advantage of all of it - micro fishing in the creek, darts, pool table, bonfire, grilling, hot tub, bags. Property was remote enough to feel peaceful while hanging out outside, also close enough to drive into Sheboygan for chartered salmon fishing, breweries, restaurants. The hosts were wonderful with clear instructions and very quick to respond to any questions. Would absolutely stay here again!

Beautiful home on a beautifully wooded street with lake view.

The place was perfect for spending the weekend hanging out with friends. The heat wasn’t turning on to begin with, but the hosts were very responsive and took multiple steps to fix it and make us comfortable.

Very nice house, ideal for us coming to town. We were 2 families with 4 kids and the place was the perfect size and convenient for all. The hot tub is a great addition, right next to the backdoor deck, very close actually from the house. Very clean and very flexible hosts, kitchen was great and the large dining table is perfect for 8 guests.

Paige was a great host who was very responsive and allowed us to check in early which was really convenient given the day. Her home was comfortable and spacious, albeit we only stayed a night, we would have happily enjoyed her home for a longer stay.

Location was perfect for what we had on our plans. I would definitely recommend BookWorm Gardens. My grandchildren enjoyed the variety of games provided.

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!

Nice place and nice people, would go back for any events I find myself at Road America.

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.

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.

This was my second work trip this year to Sheboygan from Portland, OR, and my second time staying in Brenda and Brian's absolutely lovely home. Each time I've brought 3 colleagues with me, and we've decided it's the only place we ever want to stay while in town. It's beautifully and luxuriously updated while also being super comfy, in an quiet and quaint neighborhood just a block from the beach and minutes away from the city's charming attractions and perfect home base for exploring the region. We stayed nearly a week this time out, giving us time to truly appreciate all the thoughtful details that make the home so special. Brenda is such a gracious and personable host, generously offering insider's tips on best places for food and shopping. Sheboygan is a lovely city, can't imagine a better place to enjoy time there for work or leisure. Highly recommended. Thanks again, Brenda!

We had a long term stay of about 7 weeks at Jocelyns during the first part of our Sheboygan home remodel. It was a great location and very walkable to the lake and into downtown. Exactly as described and as pictures indicated! A great place to stay to enjoy Sheboygan and all it has to offer!!

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

Nate and Kristina are wonderful hosts! The home is beautiful with all the amenities to make you feel comfortable. Everything was spotless with such homey touches, such as games to play, a fully equipped kitchen, stocked bathrooms with shampoo, conditioner, local soaps, body lotion, etc. We felt so at home and so relaxed. This was our second stay and we will be back! Thank you!!

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!

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.

Exceptional Stay in a Perfect Home! My stay at Angelia's beautiful was fantastic! From the moment I arrived, I felt warmly welcomed. The home is precisely as described, if not better. **Location:** Perfectly nestled in the woods of Black River with only a 2 minute walk to Lake Michigan. The neighborhood was surprisingly quiet and peaceful. Many people walk their dogs in the area and were quite friendly. **Cleanliness:** Spotless! This is one of the cleanest properties I've ever stayed in. Every corner of the home was immaculate and well-maintained, radiating a fresh and inviting atmosphere. **Amenities:** The home was fully equipped with everything you could possibly need to make a full Thanksgiving Feast minus the food of course. The day we arrived a care taker stopped over with a brand new standing mixer for our stay. I asked if they had a hand mixer and was told no, so I was happy to bring mine. We were so surprised when the standing mixer arrived!!

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.

Amazing! Amazing! Amazing! Such a perfect location and gorgeous home. Amber was the perfect host

The home was even nicer and more spacious than the pictures revealed.

It was nice to stay here again, centrally located for the needs of our visit. Very clean house, quiet neighborhood and enjoyed being in a cul-de-sac.