
Vacation rentals in Sheboygan
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Top-rated vacation rentals in Sheboygan
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Popular amenities for Sheboygan vacation rentals
Family friendly vacation rentals in Sheboygan

The Blue Cobb House
My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!

3-bdrm beachfront home on Lake Mich, Sheboygan WI
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!

Country Guest House - Beautiful Gardens!
Looking for a place to stay when we visited our kids for the weekend. Lots of room for the dogs to run and played pool and air hockey. Great place!!

Growe's Guest House - just like Grandma's!
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.

Stay at Sunrise LLC, Like being at Grandma's
Very friendly and welcoming hosts. The place was exceptionally clean and the kitchen was well stocked which enabled me to make a bunch of food to take to the kettle moraine state forest campground where we spent much of our free time with friends. The beds were comfortable and the home was well maintained with lots of welcoming details like bottled water in the fridge and snacks for us in the kitchen. I got the impression that everything was meticulously cared for which I really appreciated and as a result I was able to relax and enjoy my stay here.

Beachfront getaway in Sheboygan
To find a place in the middle of Sheboygan and right on the beach was fantastic. We loved the location but everything about the house was really perfect. Easy, super clean, and comfortable in every way.

Downtown Elkhart Lake - The Quintessential Suite
We absolutely love this place! Will definitely come back. The place is very comfortable; we felt right at home and had everything we needed for our stay. The hosts are very friendly and accommodating. Thank you Ryan!

Shamba on the Lake, Oostburg, WI
We have stayed at Shamba 4 times. It is an absolutely amazing spot on Lake Michigan. The home is lovely and very spacious. You could not ask for better views of the lake from inside or outside. The beach is literally right outside your door. Great spot for kids to play and great for walks too. Will definitely return again.
Dog friendly vacation rentals in Sheboygan

Norwind Ranch - Peaceful Retreat Near Road America
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!

Long Lake Chalet
The cabin itself was fantastic. Clean and accommodated our family of 6 including a pet well. The hosts were very responsive and helpful. The cabin was cozy and had great finishes. We enjoyed the fire pit and provided firewood. It was a fantastic tough having a fire going when we arrived. A couple of things to consider that are not necessarily in the owners control but helpful: the water off the dock is extremely weedy and not conducive to swimming or bobber fishing for kids. We are a tad disappointed in that. The lawn area was quite mushy given the lake was high so was practically unusable this time of year. Fishing was also pretty rough but likely due to high water and time of year. Again, time of year and not due to anything the owners can control for all the above. We enjoyed the two kayaks, canoe and paddle boat provided. The grill was a little banged up but got the job done. Overall the owners have a very well kept, cozy cabin that is very charming

House Near the Lake
Loved the place. Felt right at home. Made sure that we had everything we needed and to reach out if there was a problem! Nice and quiet neighborhood. Highly recommend and can't wait to be back!

Ellis District Urban Lake Condo
Our stay was great! Very easy to check in and out. Easy to find, very clean. We came up to fish, only recommendations we would have as people fishing is a little more table room in the living room/rooms (ex. Coffee table, bigger/extra side table) and hooks for hanging clothes that need to dry maybe by the door. Again, our stay was amazing, would definitely stay again!

Cottage @ Schoolhouse*Firepit*Petfriendly
What a lovely small house and location! I felt right at home and it was very convenient for my trip to Elkhart Lake and Road America. I only wish I was able to stay longer to enjoy all of the amenities. Highly recommend!

The Beach | Sheboygan 2Br/1 Ba
the place was great and we were so happy to be able to bring our dog with us. I was pleasantly surprised to see no dog hair from previous renters. very clean. Ashton and James were great! they were quick with all requests and super friendly. we had an emergency when we got back from our stay because my daughter left her koala lovey at the Airbnb. 😊 Ashton and James were prompt in their response and mailed the lovey to us. thank you!

Blue Barn on the Green and Farmhouse Retreat
The property was stunning, neat, and had a very homey feel to it. Everything was decorated beautifully with an old-style authentic look. Plenty of space and room offered to fit guests. Had a wonderful time with a beautiful view, highly recommend! Thank you!!!

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-
Dan is a SUPER Host! His communication is 10/10! We were given the green light to check in early however, we couldn’t due to my husband’s work schedule. Dan has a very comfortable home to stay at. We stayed with 5 adults and 2 fur babies. We were able to purchase eggs from his sons ( delicious) took A dozen home. We had the best time at the home from the pin ball machines , watching movies to hanging out with our adult kids! Can’t wait to try one of Dan’s other properties.
Vacation rentals with pools in Sheboygan

Siebkens Lockout Unit
Perfect location - easy check-in.

Country Cottage Indoor Pool HOT TUB NFL Draft ava
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.

Private Home 4 BR+2Ba, Heated Pool by Road America
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.

Resort Life 2 Queen Suite
Great place in the heart of Elkhart Lake. Close to restaurants and an easy drive to Road America.

Resort Condo on Elkhart Lake
Great stay on Elkhart Lake! Located in a central location, you can walk into town for dinner and also great lake amenities right on site. We rented a boat for the day and enjoyed the pool and beach access. We also greatly appreciate Pam being one of the few places we found that is dog friendly!

First Floor Queen with Single Pull-out
A very nice experience overall. Very responsive with questions and the location is very convenient for swimming, ice cream, getting on the lake, etc.

Road America lake house.
Jeff was a great host helping with all of our last minute needs. Extremely responsive and helpful! The house was just as described and the pool was a much needed touch after a long day. Can't recommend this place enough!!!

Private Beach, Pools & Full-Kitchen
Cute little airbnb in a private vacation rental community, but everyone is so close that it’s not very private. i wish i would’ve known beforehand that most businesses and some of the amenities such as the hot tub were still closed for the year… i think the price is steep for the off season since half the amenities weren’t available, but still had a nice retreat.
Quick stats about vacation rentals in Sheboygan
Total rentals
270 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Frequently Asked Questions
Where should I stay in Sheboygan?
Make yourself at home in Sheboygan by choosing from our most frequently booked neighborhoods. We have over 210 vacation rentals in James Madison, over 210 vacation rentals in King Park, over 270 vacation rentals in End Park, and over 210 vacation rentals in Business Drive North.
Are there vacation rentals with a dedicated workspace in Sheboygan?
Yes! Work meets play with ease at over 140 vacation rentals in Sheboygan featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Sheboygan?
Experience the best of Sheboygan with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Sheboygan?
Four-legged friends are welcome in Sheboygan. Choose from more than 70 vacation rentals for guests traveling with pets.
Do apartment rentals in Sheboygan have self check-in?
Absolutely! We offer over 10 apartment rentals with self check-in in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Sheboygan?
Sheboygan has more than 40 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Whistling Straits Golf Course
- Kohler-Andrae State Park
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