Holiday rentals in Sheboygan

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Popular amenities for Sheboygan holiday rentals

Stay near Sheboygan's top sights

John Michael Kohler Arts Center60 locals recommend
Il Ritrovo53 locals recommend
Trattoria Stefano44 locals recommend
Field to Fork44 locals recommend
Blackwolf Run Golf Course43 locals recommend
3 Sheeps Brewing Company42 locals recommend

Other great holiday rentals in Sheboygan

Superhost
Home in Sheboygan
4.67 out of 5 average rating, 21 reviews

6+ Guest Home

KyleRating, 5 stars3 months ago
Clean place, great location, great host. Very pleased with our stay, highly recommend
Guest favourite
Home in Sheboygan
5 out of 5 average rating, 16 reviews

Beautifully Renovated Historic Home at the Beach!

AmyRating, 5 stars16 months ago
Beautiful, well-appointed home with a heck of a view AND walking distance to downtown. Tricia was communicative and kind. Great experience!
Superhost
Flat in Sheboygan
4.5 out of 5 average rating, 12 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Christian DavidRating, 5 stars8 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
Guest favourite
Home in Sheboygan
4.96 out of 5 average rating, 25 reviews

State Park w/ Orchard Style Yard & Pavilion

AnnaRating, 5 stars6 months ago
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.
Guest favourite
Apartment in Sheboygan
4.93 out of 5 average rating, 85 reviews

Janelle's Dockside Condo

BarbaraRating, 5 stars5 months ago
We want to stay here every year. Beautiful condo right on the water and within walking distance to coffee shop, restaurants and parks.
Top guest favourite
Home in Sheboygan
4.95 out of 5 average rating, 42 reviews

Wander Back Inn to Sheboygan

LaurieRating, 5 stars2 weeks 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
5 out of 5 average rating, 5 reviews

Road America & Golf Retreat

NickRating, 5 stars1 month ago
Great location for a relaxing weekend with the whole family. Would gladly visit again!
Superhost
Cabin in Cascade
4.83 out of 5 average rating, 30 reviews

Lakefront Cabin on Private Lake Community

GregRating, 5 stars5 months ago
We had a fantastic stay at this cabin! It was spacious enough to comfortably accommodate three families, plus our dog and a little one. The location is perfect, nestled in a private gated community that offers a peaceful escape. The activities available were a highlight for us—fishing, paddle boarding, and kayaking kept everyone entertained and active. The scenery surrounding the cabin is absolutely beautiful, providing a perfect backdrop for our family gatherings. Overall, we had a memorable experience and would highly recommend this cabin for anyone looking for a fun and relaxing getaway with family and friends!

Quick stats about holiday rentals in Sheboygan

  • Total rentals

    270 properties

  • Nightly prices starting at

    £31 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

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sheboygan County
  5. Sheboygan