Sheboygan vacation rentals
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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
Apartment in Waldo
4.98 out of 5 average rating, 259 reviewsThe Blue Cobb House
Home in Sheboygan
4.99 out of 5 average rating, 190 reviewsWoodland Creek Retreat: explore & relax!
Home in Sheboygan
4.97 out of 5 average rating, 118 reviewsLake Michigan home with gorgeous views!
Home in Sheboygan
4.85 out of 5 average rating, 179 reviewsSerene Home One Block From Lake Michigan
Home in Plymouth
4.93 out of 5 average rating, 425 reviewsCountry Guest House - Garden Views!
Guesthouse in Oostburg
4.9 out of 5 average rating, 259 reviewsBeach House
Home in Sheboygan
4.83 out of 5 average rating, 156 reviewsHome Away From Home-One Block From Lake Michigan!
Home in Sheboygan
4.99 out of 5 average rating, 112 reviews2 Min Walk to Food, 15 to Pier! 4 Bedrooms 2K/2Q
Other great vacation rentals in Sheboygan
Home in Oostburg
4.98 out of 5 average rating, 158 reviewsRiver Ridge-HOT TUB, Games, Luxury, 8 bed, 5 STARS
Home in Manitowoc
5.0 out of 5 average rating, 102 reviewsRolling Hills Retreat~Hot Tub~KING Bed~Wood view
Apartment in Sheboygan
5.0 out of 5 average rating, 3 reviewsModern Lower Apt - One block to the Lake
Apartment in Sheboygan
4.88 out of 5 average rating, 49 reviewsOne Bdrm Apt - The Erie House near lake & downtown
Guest suite in Sheboygan
4.93 out of 5 average rating, 68 reviewsCozy 1BD RM W/ fireplace by lake
Apartment in Sheboygan
4.98 out of 5 average rating, 90 reviewsLovely modern two bedroom home with fire pit
Cottage in Sheboygan
5.0 out of 5 average rating, 68 reviewsCozy one bedroom cottage near lake Michigan!
Apartment in Sheboygan
5.0 out of 5 average rating, 38 reviewsQuaint Blast from the Past - walk to lake/8th st
Quick stats about vacation rentals in Sheboygan
Total rentals
250 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
9.4K reviews
Nightly prices starting at
$20 before taxes and fees
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 200 vacation rentals in Business Drive North, over 260 vacation rentals in End Park, and over 200 vacation rentals in James Madison.
Are there vacation rentals with a dedicated workspace in Sheboygan?
Yes! Work meets play with ease at over 130 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 house rentals in Sheboygan?
Experience the best of Sheboygan with our house rentals, starting at about $20 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 60 house rentals with a bbq area in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sheboygan have self check-in?
Absolutely! We offer over 50 house rentals with self check-in in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Sheboygan have wifi?
Absolutely! We offer over 30 condo rentals with wifi in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Sheboygan?
Sheboygan has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Condo Rentals in Sheboygan?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with self check-in, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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