Holiday rentals with a patio in Sheboygan

Castle Vineyard –HOT TUB, Theater, Golf Sim, Sauna

As seen on the cover of Haven, a luxury home magazine! This masterpiece was built over the course of seven years and is officially open to the public in 2022! For travelers who want an exclusive taste of Tuscany without the hassle of jetting across an ocean, "The Castle Vineyard" is the place to stay. The dramatic, spellbinding stone castle proudly overlooks over twenty acres of idyllic rolling hills and a gorgeous, working vineyard. Once inside, the interior does nothing to dispel the magic.

Home Away From Home-One Block From Lake Michigan!

Centrally located and pet-friendly! Walk to the beach, parks, and downtown Sheboygan. This spacious two-story home perfect for groups features flexible bedroom setups, a fully equipped kitchen, dining room, fenced backyard, and parking for up to 4 vehicles. Base pricing is competitive for small groups $15/guest per night for more than 2 guests. Close to golf courses, many family spots, restaurants, and 16 miles from Road America. Watch “Sheboygan Airbnb” on YouTube for a full walkthrough!

Vintage Farmhouse on Blueberry Hill.

Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor & outdoor), hot tub, water sports rentals, Tiki Bar, and easy access to hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

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.

The Kohler House

The Kohler House is located in the quaint village of Kohler. Our family grew up in this neighborhood and created a space to share with others that captures our love for the history and beauty that is Kohler. The home has been completely remodeled to blend a modern style with the historical architecture. It is our goal to not simply provide a space, but rather create a unique experience for our guests. We look forward to sharing our love of Kohler with you.

Spacious Home Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our 3 bedroom home near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. Send me a message to find out about our other available listings.

Cactus Corner KING Apartment

This stylish, newly remodeled upper unit is fully stocked with everything you need while away from home. Spacious and clean with a dedicated workspace and fast internet. Enjoy some fresh air on the balcony facing the pretty garden below. The building has a shared laundry area in the basement with two new washers and dryers included for guest use. There is also ample off street parking and a lovely green space.