
Holiday rentals in Sheboygan
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Top-rated holiday rentals in Sheboygan
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Sheboygan holiday rentals
Other great holiday rentals in Sheboygan
Top guest favourite

Home in Plymouth
4.96 out of 5 average rating, 171 reviewsThe 2400 sq ft Plymouth Paddock near Road America!
JuliaRating, 5 stars1 week ago
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.
Top guest favourite

Home in Sheboygan
4.96 out of 5 average rating, 182 reviewsLogan's Guest Nest
TheaRating, 5 stars4 days ago
We would definitely come back here again! You can tell that Michelle puts a lot of thought into caring for her guests. We traveled with our 5 year old who loved finding all of the kids toys, coloring books, etc. to play with. We always appreciate staying somewhere kid-friendly and this place hits it out of the park. Thanks for a great stay!
Superhost

Home in Sheboygan
4.77 out of 5 average rating, 13 reviews3 Bedroom Beach House
KatieRating, 5 stars20 months ago
Place was great! Only comment I have is the beds were too soft (I need a firmer bed) :)
Top guest favourite

Home in Oostburg
5 out of 5 average rating, 11 reviewsSurfDaze! A Lake Michigan property
JosephRating, 5 stars1 month ago
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!
Top guest favourite

Home in Glenbeulah
4.98 out of 5 average rating, 125 reviewsStay at Sunrise LLC, Like being at Grandma's
DavidRating, 5 stars6 months ago
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.
Superhost

Flat in Sheboygan
4.5 out of 5 average rating, 12 reviewsSheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Christian DavidRating, 5 stars10 months ago
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
Top guest favourite

Home in Sheboygan
4.95 out of 5 average rating, 42 reviewsWander Back Inn to Sheboygan
LaurieRating, 5 stars1 month ago
We had a great time at this place. Everything was as described. Very easy to work with and accommodating.
Guest favourite

Home in Plymouth
4.92 out of 5 average rating, 104 reviewsVintage Farmhouse on Blueberry Hill.
EllieRating, 5 stars2 months ago
We had a great stay. The place was exactly as described. It was convenient to town but had an amazing view. Michael was super responsive whenever we reached out. We would definitely stay here again and since we often come back to the same locations for races each year, we love to find places where we can be a repeat guest. This will definitely make the list in Plymouth.
Quick stats about holiday rentals in Sheboygan
Total rentals
270 properties
Nightly prices starting at
£30 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
Destinations to explore
- Rentals with lake access Sheboygan
- Rentals with a fireplace Sheboygan
- Rentals with beach access Sheboygan
- Rentals with outdoor seating Sheboygan
- Rentals with a washing machine and dryer Sheboygan
- Flat rentals Sheboygan
- Pet-friendly rentals Sheboygan
- Rentals with a patio Sheboygan
- Apartment rentals Sheboygan
- Rentals with a firepit Sheboygan
- Family-friendly rentals Sheboygan
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- Kohler-Andrae State Park
- Erin Hills Golf Course
- Whistling Straits Golf Course
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
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- West Bend Country Club
- Green Bay Country Club Sports Center
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