Ferieboliger med terrasse i Sheboygan

Castle Vineyard | Luxe Spa • Golf Sim • Theater

Stay at one of the most Wishlisted Airbnbs in the world. Featured in Men’s Health and on the cover of Haven magazine, The Castle Vineyard is a world-class destination 🍇 20-acre estate w/ vineyard, spa, & sauna 🎬 Private theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen w/ Viking appliances 🔥 Fire pit, patio, hot tub, wildlife views 🏰 "Felt like royalty... every detail was magical" 🎉 Entire property is yours — guests may inquire about our exclusive Tasting Room for special events

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!

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

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!

Recombobulation Station-Locally Owned Surf Escape

Our reviews speak volumes! Blocks from North Beach+Riverfront+8th St Kitchen is stocked and ready for your cooking needs. Main Bedroom - Luxurious pillow top mattress + Blackout Blinds + Ceiling Fan 15min-Kohler Spa & Whistling Straits 20min-Road America 1hr-Green Bay/Lambeau Field Military Discount 🪖 🙏 Clean & Comfortable-Continuously maintained and updated. Highly rated and reviewed. We love this town and we love hosting. If you need any local recommendations we have plenty!

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.

The Sheboygan Foodie Flat

Schnazzy upper flat in the heart of Sheboygan’s Eastside. Walk to Lake Michigan Beaches, Riverfront, Uptown and Downtown. Enjoy the newly renovated 2nd floor of an 1893 historic rambler, with lots of natural light. -Desirable Eastside, with walkable neighborhoods. -Large Italian tile walk-in shower with Kohler fixtures. -Fully equipped kitchenette with microwave, convection oven, two-burner hot plate, Keurig, coffee pot & toaster. -New furnishings -Sheboygan Foodie Guidebook

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.

Harbor View KING 2BDR Suite

Great location in downtown Sheboygan. Walking distance to shops restaurants and bars. Nice quiet street with ample free parking, right by the beach, ice cream shop and boardwalk. Two king size beds, fully stocked and renovated kitchen, and huge in unit washer and dryers. Your family will be close to everything when you stay at this beautiful, centrally-located two bedroom apartment.