Sheboygan vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Sheboygan
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Sheboygan vacation rentals
Other great vacation rentals in Sheboygan
Cottage in Random Lake
4.82 out of 5 average rating, 62 reviewsPrivate 3 bedroom lake house
Home in Plymouth
4.97 out of 5 average rating, 154 reviewsThe 2400 sq ft Plymouth Paddock near Road America!
Home in Sheboygan
5 out of 5 average rating, 25 reviewsThe Riverbed
Home in Sheboygan
4.77 out of 5 average rating, 13 reviews3 Bedroom Beach House
Home in Oostburg
5 out of 5 average rating, 6 reviewsFall & Holiday dates available at Surfdaze!
Home in Sheboygan
4.95 out of 5 average rating, 37 reviewsWander Back Inn to Sheboygan
Home in Elkhart Lake
4.89 out of 5 average rating, 64 reviewsElkhart Lake Village house
Home in Belgium
5 out of 5 average rating, 51 reviewsGorgeous New Construction Lake House
Quick stats about vacation rentals in Sheboygan
Total rentals
240 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
9.7K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
120 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 Business Drive North, over 260 vacation rentals in End Park, and over 210 vacation rentals in James Madison.
Are there vacation rentals with a dedicated workspace in Sheboygan?
Yes! Work meets play with ease at over 120 vacation rentals in Sheboygan featuring dedicated workspaces. Stay connected and productive 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.
How much does it cost to stay in condo rentals in Sheboygan?
Experience the best of Sheboygan with our condo rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Sheboygan have a gym?
Absolutely! We offer over 10 house rentals with a gym in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sheboygan have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
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.
Do apartment rentals in Sheboygan have wifi?
Absolutely! We offer over 50 apartment rentals with wifi in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Sheboygan?
Sheboygan has more than 110 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Sheboygan?
Enhance your stay in our House Rentals with the most popular amenities: over 130 homes with wifi, over 50 homes with self check-in, over 50 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Madison Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Green Bay Vacation rentals
- Oshkosh Vacation rentals
- Grand Haven Vacation rentals
- Lake Wisconsin Vacation rentals
- Appleton Vacation rentals
- Muskegon Vacation rentals
- Silver Lake Vacation rentals
- Fox Lake Vacation rentals
- Chicago Vacation rentals
- Rentals with beach access Sheboygan
- Rentals with a fireplace Sheboygan
- Rentals with lake access Sheboygan
- Apartment rentals Sheboygan
- Rentals with a fire pit Sheboygan
- Monthly Rentals Sheboygan
- Rentals with outdoor seating Sheboygan
- Pet-friendly rentals Sheboygan
- House rentals Sheboygan
- Rentals with a patio Sheboygan
- Rentals with a washer and dryer Sheboygan
- Condo rentals Sheboygan
- Kid-friendly rentals Sheboygan
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes