Holiday rentals with a patio in Sheboygan

The Random Cabin (On Random Lake)

Suprising Waterfront Cozy Unique Rustic Modern. These all describe the Random Cabin. In the small inviting village of Random Lake sits a small but mighty house. 2 bedrooms, beautiful kitchen, tree fort style loft, 2nd living/kid room w/ arcade & pinball. Everything you could want. Fish off the pier or use our kayaks to explore the lake. Ride our bikes around town & then cuddle up in front of the fireplace. The village beach is only a few blocks away, so is the bustling downtown. Memories await

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!

Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar

Slow down at Fraser Fir log cabin, built in 1958 on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

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!

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.

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.

Forest cabin near Kohler-Andrae w/ hot tub

Welcome to Pine Dunes Cabin, a cozy forest retreat just steps from Lake Michigan - perfect for relaxed group getaways year-round. Tucked among trees on a quiet stretch of land, this cabin blends space, comfort, and nature. - Sleeps up to 10 | 4 bedrooms | 7 beds | 3 baths - Seasonal hot tub (Nov–Apr) & outdoor fire pit - 3 decks + large three-season room - Fully equipped kitchen & spacious dining - Smart TVs, WiFi & loft hangout space - Beach essentials & easy lake access

Luxury downtown retreat w/ balcony

Welcome to a thoughtfully designed downtown retreat where comfort, art, and location come together. This private coach house offers an inviting place to unwind while staying close to everything Sheboygan has to offer. - Sleeps 4 | 2 bedrooms | 3 beds | 1 bath - Entire guesthouse w/ private entrance - Open-concept living area w/ TV - Fully equipped kitchen & dining table - Patio or balcony for fresh air - Walkable downtown location near dining & riverfront

Vibrant home w/ beach & lake access

Warm, welcoming, and thoughtfully designed, this entire home in Sheboygan’s Ellis Historic District puts you close to the lake, downtown, and everyday comforts while offering a relaxing place to unwind. - Sleeps 8 | 3 bedrooms | 4 beds | 2.5 baths - Bright open layout w/ chef’s kitchen & dining space - Electric fireplace & cozy living area - Private patio & backyard w/ BBQ - Beach essentials & bikes included - Walkable to beach, riverfront & downtown

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for families or groups. Enjoy a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. With 7 beds, a fully stocked kitchen, in-unit washer/dryer, and stylish living spaces, comfort and convenience come standard. Your relaxing lakeside getaway starts here.

Recombobulation Station-Locally Owned Surf Escape

We love this town and we love hosting. If you need any local recommendations we have plenty! 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.