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Sheboygan Vacation Rentals

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    Travelers to Sheboygan are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 18 Rentals in Sheboygan
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    Lake Shore House on Lake Michigan! Dog Friendly!1 / 7
    (15)Excellent
    Sheboygan
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    REMODELED HOUSE ON LAKE MICHIGAN1 / 18
    (2)Very good
    Sheboygan
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lake Michigan by Whistling Straits1 / 17
    (1)Excellent
    Sheboygan
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sheboygan
    2 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Patio
    • Grill
    • Waterfront
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the gorgeous bluffs of Sheboygan's Lake Michigan waterfront! Our lakefront home is perfect for a romantic getaway, girls weekend, golf trip, or fun family vacation year round. Close to town, shops, bars & restaurants! Our eastern facing, sun-filled lake house with picture windows is...
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    Sheboygan, Wisconsin 53081
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 9
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    Lake Orchard Farm Cottage1 / 24
    (4)Excellent
    Sheboygan
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Parking
    • Internet Access
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 17, 2016
    I spent the weekend with my family of 8 adults. The room sizes were perfect. The Beds very comfortable. Plenty of showers and bathrooms. No one had to wait. Dinning...
    Reviewed September 16, 2015
    Lake Orchard Cottage was just the perfect place for us. Space for all, and well equipped. The weather was perfect. What more could you ask for?
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    About this property
    Relax and recharge at our unique historical leisure property on the shores of Lake Michigan. Come stay on our sixth generation farm and experience a vacation you will never forget. Exceptional hospitality and multiple on site leisure activities await you. Just 15 miles north of Sheboygan and one...
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    Sheboygan, Wisconsin 53083
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Historic Mansion Right on Lake Michigan!1 / 19
    (1)Excellent
    Sheboygan
    9 Bedrooms, 9 Bathrooms, Sleeps 25 Quick View
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    • Patio
    • Washer
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2015
    This beautifully positioned stately home within walking distance to town and the lake front is an experience everyone should have. From start to finish the owner makes renting...
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    About this property
    The 10,000 square foot Castino Lakeview Mansion sits high atop a bluff with breathtaking views of Lake Michigan. It's just steps down to the expansive beach and marina, with sand volleyball nets and fire pits. The house combines the feel of yesteryear's opulence with all the modern amenities....
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    Sheboygan, Wisconsin 53081
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 25
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    BEACHSIDE GETAWAY1 / 12
    (1)Very good
    Sheboygan
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    2 bed, 1 bath cute condo. Clean. 1 car garage with tight driveway. Beach and city park a jump, skip and hop away. On a windy day there were kite surfers we watched from front...
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    About this property
    Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a small building. You can listen to the waves or walk just a few feet and have the sand under your feet. This condo features...
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    Sheboygan, Wisconsin 53081
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sheboygan
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms and 1.5 Baths in this two story brick home. Located about one mile south of downtown Sheboygan on a bluff overlooking the beautiful Lake Michigan. Just enter Sheboygan, WI 53081 in any search engine and you can easily figure out how far things are away. There is no direct access to the...
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    Sheboygan, Wisconsin 53081
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sheboygan
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Yard
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2200 sq ft cozy house is perfectly located within minutes from Lake Michigan,Road America,Memorial hospital, and three highly rated golf courses (Whistling Straits 6 miles 10 min drive, Blackwolf Run 5.9 miles 13 min drive, and the The Bull 9 miles 15 min drive). Downtown Sheboygan is a 5...
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    Sheboygan, Wisconsin 53083
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sheboygan
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Parking
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautifully, remodelled 4-bedroom home. It is close to Sheboygan's best restaurants and less than a 3 minutes drive from Lake Michigan, Kohler Resort & Spa and Blue Harbor Resort. The master bedroom is an en suite with a dual access bathroom and a queen sized bed. On the upper floor is...
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    Location Information
    Sheboygan, Wisconsin 53081
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Aspen House - Private, peaceful country home near Elkhart Lake1 / 32
    (12)Excellent
    Elkhart Lake
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Private Yard
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2018
    Its an awesome place to rent. We were 2 couples that came for the historic car races at Elkhart Lake. When we arrived a bottle of wine & 4 wine glasses were on the table for...
    Reviewed August 13, 2017
    We loved this house. Inside the house is beautiful and well appointed, everything one could need. We really enjoyed the quiet and the beautiful view out of each window. Nothing...
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    About this property
    Get away from it all in my quiet and very private country home near Elkhart Lake, WI. You'll be minutes away from Road America, the scenic Kettle Moraine State Forest, the Sheboygan Marsh and lookout tower, a public beach, three world famous golf courses (two PGA Women's Open tournaments were held...
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    Elkhart Lake, Wisconsin 53020
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Oostburg
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aunt Dot’s accommodates 6 overnight guests, and is charming by all accounts. It feels restful the minute you walk in the door. There are 3 bedrooms, 2 baths, a kitchen ready to use, and a living room with a beautiful stone fireplace, well-stocked bookshelves and a picture window overlooking Lake...
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    Oostburg, Wisconsin 53070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Glenbeulah
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedroom, 2 Bathroom, Sleeps 7 Make yourself comfortable in this large Victorian home! It has four spacious bedrooms with two full baths and is the ultimate family retreat or vacation getaway with a group of friends. Master has a king size bed, other bedrooms consist of a queen size beds, and...
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    Glenbeulah, Wisconsin 53023
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Glenbeulah
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our one bedroom rental is located on an amenity-filled resort in Glenbeulah! The private bedroom has a queen bed and flat screen TV.The living room features a full size sofa sleeper, an electric fireplace, a 40' flat screen TV with cable, A/C, the kitchen is fully equipped and includes cookware...
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    Glenbeulah, Wisconsin 53023
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    RESToration House1 / 15
    (1)Very good
    Cleveland
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Parking
    • Private Yard
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautiful location near Beautiful Lake Michigan. 3/4 mile walk or bike to the Lake. Bikes for use available. House is loacted 5 minutes from Whistling straits, great place to stay for PGA tour! Other nearby attractions: Destination Kohler- 18minutes Lambeau Field (Home of Green Bay...
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    Cleveland, Wisconsin 53015
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Elkhart Lake
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Monte Carlo, presented by Luxury Motor Courts, offers guests peaceful luxury and exclusivity. The villa is located less than 1 mile from Road America Race Track, mere minutes from Downtown Elkhart Lake, and less than 15 miles from renowned golf courses. Monte Carlo is outfitted with all of the...
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    Elkhart Lake, Wisconsin 53020
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oostburg
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the breathtaking sunrises and awe-inspiring views of Lake Michigan from our year-round home. Our private and quiet setting is a relaxing getaway for two or a great family vacation. Our architecturally designed mid century year-round home has breathtaking views of the lake from every room from...
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    Location Information
    Oostburg, Wisconsin 53070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elkhart Lake
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury Motor Courts introduces The Monaco. The Monaco offers four lock-out suites fit for the race team, guy's golf outing, or couple's weekend away. Your most luxurious vacation yet is conveniently located 1 minute from the world renowned Road America and unique downtown Elkhart Lake, Wisconsin....
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    Location Information
    Elkhart Lake, Wisconsin 53020
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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