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Holiday rentals in Sheboygan County

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Top-rated holiday rentals in Sheboygan County

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

Sophisticated  Manor for the Holidays
SUPERHOST
Entire residential home · 8 guests · 4 beds · 4 bathrooms
Sophisticated Manor for the HolidaysThis home was built for entertaining and what better time to do so than the Holiday season! Modern & Timeless Chic. Enjoy the expansive 4,500 square feet of elegance and character that adorns this well-appointed home. Complete with 3 bedrooms, 3 full baths and 2 half baths, a den with a queen sleeper sofa, & many different areas for entertainment throughout. Situated between the lakefront and downtown. Just a 15 minute drive to Whistling Straights, and within an hour of Milwaukee and Green Bay.
Lakefront Charmer Just Listed, Cheery 2021 Remodel
Entire residential home · 12 guests · 6 beds · 2.5 bathrooms
Lakefront Charmer Just Listed, Cheery 2021 RemodelThis 2600 sqft lakefront home is holiday ready for families friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. DIne with seating and service for 12 after cooking in the spacious bright kitchen. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. 2 miles to downtown with shops and restaurants . Walk to nearby beaches or descend to waters edge from the backyard.
Bright & clean Studio in peaceful countryside
Entire guest house · 4 guests · 1 bed · 1 bathroom
Bright & clean Studio in peaceful countrysideEnjoy the peaceful countryside in our cozy Studio Guesthouse! The Studio is a separate 375 sq. foot building on our property (situated approx. 75' from our home) that you will have all to yourself. If you love nature and you're looking for a quiet retreat in the hilly Kettle Moraine area, this is the perfect little haven for you!

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Popular amenities for Sheboygan County holiday rentals

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

Other great holiday rentals in Sheboygan County

SUPERHOST
  1. Entire rental unit
  2. Sheboygan
The Beach | Sheboygan 2Br/1 Ba
₹7,553 per night
SUPERHOST
  1. Entire residential home
  2. Sheboygan
Walk to beach, pier, restaurants, shops!
₹11,743 per night
SUPERHOST
  1. Entire residential home
  2. Kohler
The Kohler House
₹12,813 per night
SUPERHOST
  1. Entire cottage
  2. Oostburg
Sandalwood Cottage - 300 Feet From Lake Michigan
₹9,360 per night
SUPERHOST
  1. Entire residential home
  2. Oostburg
Lake Michigan Beach Home by Frank Lloyd Wright pro
₹17,299 per night
SUPERHOST
  1. Entire residential home
  2. Plymouth
Sage Cottage
₹8,337 per night
  1. Entire apartment
  2. Sheboygan
2BR Main Floor Beach/Lake Condo *NO EXTRA FEES*
₹11,296 per night
SUPERHOST
  1. Entire apartment
  2. Sheboygan
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
₹16,138 per night
SUPERHOST
  1. Entire rental unit
  2. Sheboygan
Downtown Walk-up
₹6,132 per night
  1. Entire cottage
  2. Plymouth
Vintage Farmhouse on Blueberry Hill.
₹10,468 per night
SUPERHOST
  1. Entire place
  2. Elkhart Lake
Schoolhouse Straight/Main House
₹15,061 per night
SUPERHOST
  1. Entire rental unit
  2. Sheboygan
Heart of Downtown Sheboygan
₹9,715 per night