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Vacation 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.

Guest favourite
Home in Sheboygan
Dog Friendly Blue Door Cottage / Fully Fenced Yard
Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.
30 Sep – 7 Oct
$191 NZD per night
4.96 out of 5 average rating, 141 reviews
Guest favourite
Apartment in Sheboygan
Cozy Sheboygan Upper
We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.
14–21 Feb
$151 NZD per night
4.92 out of 5 average rating, 384 reviews
Guest favourite
Home in Sheboygan
Beachfront getaway in Sheboygan
One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.
16–23 Apr
$402 NZD per night
4.93 out of 5 average rating, 168 reviews

Popular amenities for Sheboygan holiday rentals

Stay near Sheboygan's top sights

Blue Harbor Resort27 locals recommend
Bookworm Gardens31 locals recommend
Black Pig19 locals recommend
Parker John's BBQ & Pizza - Sheboygan22 locals recommend
Texas Roadhouse3 locals recommend
John Michael Kohler Arts Center60 locals recommend

Other great holiday rentals in Sheboygan

Guest favourite
Cottage in Oostburg
Sandalwood Cottage - 300 Feet From Lake Michigan
15–22 Feb
$259 NZD per night
4.97 out of 5 average rating, 225 reviews
Guest favourite
Guesthouse in Oostburg
Beach House
25 Oct – 1 Nov
$401 NZD per night
4.9 out of 5 average rating, 248 reviews
Superhost
Guest suite in Sheboygan
Modern + Minimalist 1BR Near Lakeshore Apartment!
21–28 Oct
$151 NZD per night
4.87 out of 5 average rating, 23 reviews
Guest favourite
Villa in Sheboygan
Just 75 steps from the shore of Lake Michigan
21–28 Jan
$229 NZD per night
4.93 out of 5 average rating, 56 reviews
Guest favourite
Apartment in Sheboygan
Modern Upper Apt - Steps from Lake Michigan
13–20 Apr
$253 NZD per night
5.0 out of 5 average rating, 76 reviews
Guest favourite
Home in Sheboygan
Spacious MCM Vibe Near Lake MI w/ Fire Pit
28 Dec – 4 Jan
$217 NZD per night
4.92 out of 5 average rating, 59 reviews
Guest favourite
Guest suite in Sheboygan
Cozy 1BD RM W/ fireplace by lake
19–26 May
$179 NZD per night
4.92 out of 5 average rating, 59 reviews
Guest favourite
Apartment in Sheboygan
One Bdrm Apt - The Erie House near lake & downtown
13–20 Feb
$179 NZD per night
4.87 out of 5 average rating, 46 reviews
Guest favourite
Loft in Sheboygan
Spacious/stylish, 2br loft
15–22 May
$255 NZD per night
4.97 out of 5 average rating, 74 reviews
Guest favourite
Home in Sheboygan
Relaxing Sheboygan/Kohler Getaway
10–17 May
$233 NZD per night
5.0 out of 5 average rating, 61 reviews
Guest favourite
Condo in Sheboygan
South Pier River Walk Condo with Spectacular Views
20–27 Mar
$366 NZD per night
4.97 out of 5 average rating, 67 reviews
Guest favourite
Home in Sheboygan
4 Bedroom Beachfront Condo
20–27 Oct
$783 NZD per night
4.92 out of 5 average rating, 12 reviews

Quick stats about holiday rentals in Sheboygan

Total rentals

250 properties

Rentals with dedicated workspaces

120 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

9.2K reviews

Nightly prices starting at

$32 NZD before taxes and fees

Destinations to explore

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