Skip to content

Vacation rentals in Sheboygan County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Sheboygan County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Sandalwood Cottage - 300 Feet From Lake Michigan
SUPERHOST
Entire cottage · 6 guests · 3 beds · 1 bath
Sandalwood Cottage - 300 Feet From Lake MichiganA hideaway one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan on a private drive. Just south of Sheboygan, Whistling Straits & PGA golf courses. Ryder Cup 2021, is a 20 minute drive. Also close to Elkhart Lakes - Road America, Charter Fishing, Local 5 Star Restauranteurs, Boutiques & Wedding Venues. We are 2 hrs. & 10 min away from Chicago. 45 min from Milwaukee. 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.
Beach/Lake Condo: Waves of Happiness--Unit #2 main
Entire condominium (condo) · 4 guests · 2 beds · 1 bath
Beach/Lake Condo: Waves of Happiness--Unit #2 mainYou will see & hear the beauty of Lake Michigan during your stay at this newly renovated first floor condo. A deck to the north allows views of the magnificent Blue Harbor Resort on the water. The south deck gives more amazing views of the lake, plus an adjacent park just steps out the back door. You can stroll the beach,walk the River Boardwalk; or tour our historical downtown full of shops, art opportunities, and exquisite restaurants, all walkable from the condo.
River Home Getaway with River Access
SUPERHOST
Entire residential home · 8 guests · 4 beds · 2 baths
River Home Getaway with River AccessEnjoy your getaway in the comfort of the River Home. With the Sheboygan River flowing through your backyard and living spaces stylishly decorated, the scene is set for a truly remarkable vacation. The eat in kitchen is equipped with all the necessities to whip up a delightful meal. The family room has a variety of board games as well as a smart TV for entertainment. The space is complete with four well appointed bedrooms. You are welcome to bring your own boat and use the private boat slip.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Sheboygan County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Sheboygan County

SUPERHOST
  1. Entire residential home
  2. Sheboygan
Dog Friendly Blue Door Cottage
  1. Entire rental unit
  2. Sheboygan
2 bedroom unit with full Lake Michigan views
  1. Entire cottage
  2. Sheboygan
Cozy one bedroom cottage near lake Michigan!
SUPERHOST
  1. Entire rental unit
  2. Sheboygan
Downtown Walk-up
SUPERHOST
  1. Entire residential home
  2. Sheboygan
Group Fun @ Private Wooded Beachfront Home
SUPERHOST
  1. Entire condominium (condo)
  2. Sheboygan
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
SUPERHOST
  1. Entire residential home
  2. Plymouth
Wyatt's Country Home - Sparkling Clean!
SUPERHOST
  1. Entire guesthouse
  2. Sheboygan
Nautical Themed Guest Suite, Kohler Food & Wine
  1. Entire loft
  2. Sheboygan
Wis. Get-away, spacious/stylish 2br loft, parking
SUPERHOST
  1. Entire residential home
  2. Plymouth
Serene Lake Front Cottage.. Walk to Road America
SUPERHOST
  1. Entire residential home
  2. Plymouth
Sage Cottage
SUPERHOST
  1. Entire rental unit
  2. Sheboygan
Heart of Downtown Sheboygan