Holiday houses in Sheboygan

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Top-rated holiday rentals in Sheboygan

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Guest favourite

Rental unit in Sheboygan

4.98 out of 5 average rating, 113 reviews

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!

Guest favourite

Cottage in Oostburg

4.97 out of 5 average rating, 240 reviews

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.

Guest favourite

Home in Howards Grove

4.95 out of 5 average rating, 159 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

Guest favourite

Rental unit in Kohler

5 out of 5 average rating, 100 reviews

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Guest favourite

Townhouse in Sheboygan

4.96 out of 5 average rating, 133 reviews

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.

Guest favourite

Rental unit in Sheboygan

4.98 out of 5 average rating, 106 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Guest favourite

Home in Sheboygan

4.96 out of 5 average rating, 165 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Guest favourite

Rental unit in Sheboygan

4.92 out of 5 average rating, 431 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Guest favourite

Home in Sheboygan

4.94 out of 5 average rating, 177 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Superhost

Guesthouse in Sheboygan

4.83 out of 5 average rating, 390 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 128 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Guest favourite

Rental unit in Sheboygan

4.84 out of 5 average rating, 280 reviews

Sheboygan Surf House "The Elbow"

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our newly remodeled Urban living oasis is a studio and a half that is conveniently located in the heart of downtown, just steps from renown bars and restaurants and only blocks to Lake Michigan, The Sheboygan River, South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake or leisure time SSH is perfect for you.