Holiday rentals with a patio in Sheboygan County

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

Storybook Home - 1 mi to Lake & Downtown Sheboygan

Welcome to The Fox & Folly Inn 🦊 —a unique whimsical retreat. Perfect for families and those who are kids at heart! 🖼️ Creative and cozy home with art and murals. 🦊🐰🦉Themed with original characters. Audio stories & endless charm! 🛏️ Master Bedroom - King Bed 🛋️ 2nd Bedroom - Bunk Bed = Full Lower, Twin Upper 🛌 Sleeps 5 🛁 1 Full Bathroom - Towels, Hair Dryer+ 🍽️ Fully Stocked Kitchen 🅿️ Off-Street Parking 🏖️Minutes from the beach & Bookworm Gardens 📖Your storybook adventure awaits!

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!

The perfect location!

You will be close to everything when you stay at this 1930s home. Walk three blocks west to Sheboygan's historic downtown to find shops, restaurants, theaters, museums, and a local farmer’s market. Walk two blocks east to the beach, walking/biking trail, marina, and parks. Free street parking, 1-stall attached garage, reliable wifi. All three bedrooms and full bathroom are upstairs. Washer/dryer and 1/2 bath are in the basement. Three window AC units in the summer. Kitchen has basic amenities.

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.

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.

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

Outdoor Sauna | 6-BRs | Kohler-Andrae

🏖️ Private Sandy Beach on Lake Michigan 🔥 Waterfront Fire Pit for Cozy Evenings 🧖‍♀️ New Lakeview Sauna 🪟 Open-Concept Living with Wall-to-Wall Lake Views 🛏️ 6 Bedrooms – Sleeps Large Groups Comfortably 🍳 Fully Equipped Kitchen & Spacious Dining Area ☀️ Expansive Deck for Coffee, Sun & Scenic Relaxation 🌲 Wooded, Tranquil Neighborhood Near Kohler-Andrae State Park 🚗 Minutes to Sheboygan, Kohler, & Road America 🔐 Private Home with Seamless Self Check-In

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

Sheboygan Riverside Condo

Experience the Malibu of the Midwest in this stunning 2-bedroom retreat! The king suite offers a private balcony with a cozy fireplace overlooking the serene Sheboygan River. The second bedroom features two queen beds, perfect for families or friends. Enjoy an open-concept living space, modern kitchen, and easy access to Sheboygan's best attractions. With a 2-car garage and nearby conveniences, this is your ideal getaway spot!

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.