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
Cottage in Oostburg
Sandalwood Cottage - 300 Feet From Lake Michigan
A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.
8 – 15 Nov
4.97 out of 5 average rating, 227 reviews
Guest favourite
Apartment in Sheboygan
Modern Upstairs Apt - Steps from Lake Michigan
Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!
31 Jan – 7 Feb
5.0 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Sheboygan
Quaint Blast from the Past - walk to lake/8th st
Renovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our "Blast from the Past" as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!
15 – 22 Apr
5.0 out of 5 average rating, 33 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
Guest suite in Sheboygan
Cozy 1BD RM W/ fireplace by lake
30 Dec – 6 Jan
4.92 out of 5 average rating, 62 reviews
Guest favourite
Apartment in Sheboygan
Lovely modern two bedroom home with fire pit
17 – 24 Dec
4.98 out of 5 average rating, 87 reviews
Guest favourite
Condo in Sheboygan
South Pier River Walk Condo with Spectacular Views
27 Apr – 4 May
4.97 out of 5 average rating, 68 reviews
Guest favourite
Condo in Sheboygan
Downtown Beachside Condo with Lake Michigan Views
9 – 16 Nov
4.99 out of 5 average rating, 97 reviews
Guest favourite
Condo in Sheboygan
Urban Townhouse
19 – 26 Dec
5.0 out of 5 average rating, 42 reviews
Guest favourite
Apartment in Sheboygan
One Bdrm Apt - The Erie House near lake & downtown
3 – 10 Aug
4.87 out of 5 average rating, 46 reviews
Guest favourite
Home in Sheboygan
The perfect location!
15 – 22 Jan
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Sheboygan
Relaxing Sheboygan/Kohler Getaway
1 – 8 July
5.0 out of 5 average rating, 62 reviews
Guest favourite
Condo in Sheboygan
Janelle's Dockside Condo
25 Aug – 1 Sept
4.95 out of 5 average rating, 57 reviews
Guest favourite
Townhouse in Sheboygan
Danz Sheboygan Retreat. Newly Remodeled in 2021.
10 – 17 May
4.94 out of 5 average rating, 80 reviews
Guest favourite
Home in Sheboygan
ClaraVida - Cheerful 1 Bed/2 Bath Near Beach
12 – 19 July
4.94 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Sheboygan
A Wave From It All! - Lake Condo
25 Aug – 1 Sept
4.96 out of 5 average rating, 25 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

$30 AUD before taxes and fees

Destinations to explore

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