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.

Guest favorite
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.
Jan 30 – Feb 6
$130 per night
4.97 out of 5 average rating, 227 reviews
Guest favorite
Townhouse in Sheboygan
Family Friendly Riverfront Escape|HUGE Game Room
Welcome to The WAVE – your ideal family friendly retreat nestled along the scenic Sheboygan River, just minutes from the beaches of Lake Michigan. As you step into The WAVE, you'll be greeted by a tastefully designed interior featuring LUX furnishings that exude both style and coziness. The accommodations include a King Suite with a riverfront balcony and a Guest Room with 2 queen beds. Entertainment is taken to a whole new level with our 500 sq ft game room with a 130-inch projection screen.
Feb 1 – 8
$103 per night
4.97 out of 5 average rating, 113 reviews
Superhost
Home in Sheboygan
Dog Friendly Cozy Cottage Rental on Lake Michigan!
Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals, Blue Harbor Rentals, Road America Rentals, Kohler Art Center Rentals, Black Wolf Run Rentals, Lake Michigan Fishing Charters Rentals, Green Bay Packer Rentals, Door County Rentals, Honeymoon Rentals, Women's Weekend Rentals, Lake Michigan Sunrise Rentals, Dog Friendly Rentals, Winter Rentals. Dog Friendly Rentals, Sheboygan, Wisconsin Rentals, Saugatuck, Michigan Rentals, New Buffalo, Michigan Rentals
Dec 10 – 17
$133 per night
4.86 out of 5 average rating, 180 reviews

Popular amenities for Sheboygan vacation 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 vacation rentals in Sheboygan

Guest favorite
Home in Howards Grove
Spacious lower level priv entrance no cleaning fee
Nov 25 – Dec 2
$95 per night
4.95 out of 5 average rating, 151 reviews
Guest favorite
Guesthouse in Oostburg
Beach House
Jan 27 – Feb 3
$199 per night
4.9 out of 5 average rating, 252 reviews
Guest favorite
Home in Sheboygan
Serene Home One Block From Lake Michigan
Dec 9 – 16
$174 per night
4.85 out of 5 average rating, 175 reviews
Guest favorite
Place to stay in Elkhart Lake
Cottage @ Schoolhouse*Firepit*Petfriendly
Apr 6 – 13
$139 per night
4.96 out of 5 average rating, 182 reviews
Guest favorite
Home in Sheboygan
Woodland Creek Retreat: explore & relax!
May 5 – 12
$239 per night
4.99 out of 5 average rating, 190 reviews
Guest favorite
Apartment in Sheboygan
Modern Upstairs Apt - Steps from Lake Michigan
Apr 18 – 25
$115 per night
5.0 out of 5 average rating, 81 reviews
Guest favorite
Loft in Sheboygan
Spacious/stylish, 2br loft
Mar 20 – 27
$103 per night
4.97 out of 5 average rating, 74 reviews
Guest favorite
Guest suite in Sheboygan
Cozy 1BD RM W/ fireplace by lake
Dec 30 – Jan 6
$86 per night
4.92 out of 5 average rating, 62 reviews
Guest favorite
Apartment in Sheboygan
Lovely modern two bedroom home with fire pit
Sep 25 – Oct 2
$113 per night
4.98 out of 5 average rating, 87 reviews
Guest favorite
Apartment in Sheboygan
Quaint Blast from the Past - walk to lake/8th st
Apr 15 – 22
$108 per night
5.0 out of 5 average rating, 33 reviews
Guest favorite
Cottage in Sheboygan
Cozy one bedroom cottage near lake Michigan!
Jun 10 – 17
$118 per night
5.0 out of 5 average rating, 67 reviews
Guest favorite
Apartment in Sheboygan
One Bdrm Apt - The Erie House near lake & downtown
Sep 30 – Oct 7
$80 per night
4.87 out of 5 average rating, 46 reviews

Other great vacation rentals in Sheboygan

Guest favorite
Condo in Sheboygan
Urban Townhouse
Dec 20 – 27
$151 per night
5.0 out of 5 average rating, 42 reviews
Superhost
Apartment in Sheboygan
Lovely 1 Bedroom Serviced apartment in Sheboygan
Mar 25 – Apr 1
$99 per night
4.9 out of 5 average rating, 49 reviews
Guest favorite
Townhouse in Sheboygan
Danz Sheboygan Retreat. Newly Remodeled in 2021.
May 11 – 18
$102 per night
4.94 out of 5 average rating, 80 reviews
Guest favorite
Home in Sheboygan
Quaint and Cozy home near beach on Lake Michigan
Nov 17 – 24
$91 per night
4.89 out of 5 average rating, 53 reviews
Guest favorite
Home in Sheboygan
The Suncatcher - Steps from Lake Michigan
Apr 21 – 28
$139 per night
4.95 out of 5 average rating, 19 reviews
Guest favorite
Home in Sheboygan
Spacious MCM Vibe Near Lake MI w/ Fire Pit
Aug 19 – 26
$138 per night
4.92 out of 5 average rating, 63 reviews
Guest favorite
Apartment in Sheboygan
North 7th Place - Entire Unit- 2 bedrooms
Feb 13 – 20
$112 per night
4.96 out of 5 average rating, 27 reviews
Guest favorite
Condo in Sheboygan
Downtown Beachside Condo with Lake Michigan Views
Nov 20 – 27
$162 per night
4.99 out of 5 average rating, 97 reviews
Guest favorite
Home in Waldo
Perfect Winter Getaway!
Oct 23 – 30
$111 per night
4.98 out of 5 average rating, 55 reviews
Guest favorite
Apartment in Sheboygan
Peaceful apartment by the lake
Jul 8 – 15
$104 per night
4.95 out of 5 average rating, 20 reviews
Guest favorite
Home in Sheboygan
Grammy’s house in a quiet and convenient location
Apr 7 – 14
$144 per night
4.93 out of 5 average rating, 29 reviews
Guest favorite
Guesthouse in Sheboygan
The Studio
Sep 11 – 18
$122 per night
5.0 out of 5 average rating, 9 reviews

Quick stats about vacation 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

$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 James Madison, over 200 vacation rentals in Business Drive North, and over 260 vacation rentals in End Park.

  • 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 apartment rentals in Sheboygan?

    Experience the best of Sheboygan with our apartment rentals, starting at about $50 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 condo rentals in Sheboygan have self check-in?

    Absolutely! We offer over 10 condo 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 60 apartment 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 40 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Sheboygan?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with self check-in, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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