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

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.

Recombobulation Station-In The Heart of Sheboygan!

Highly Rated 2 bedroom Historic Home. Experience the charm of this beautifully preserved home while enjoying your private completely renovated 2nd-floor unit. Perfectly nestled in the walkable Ellis Historic District We are local owners who love sharing our town • Blocks from North Beach+Riverwalk+8th St • Record Player+curated vinyl • Stocked Kitchen+Luxurious pillow-top main bed •5 min:Weill Center+Arts Center •15 min:Kohler Spa+Whistling Straits •20 min:Road America •1 hr:Lambeau Field

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.

Private 3 bd country home 2 miles N of Kohler WI

Summer is coming! 🌞 Book Now! Private newly built house on 25 acres-2 miles North of Kohler. Good Pets stay free, plenty of room to run! Just a short drive to Whistling Straits, Road America and Lake Michigan. A great location to enjoy all Sheboygan County has to offer. Bring the entire family and the dogs. Enjoy your day and return to a spacious home with a newly added putting green and BBQ area. Surrounded by growing fields, many deer, multiple birds and a gorgeous sunset every night.

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.

Lake Front Cottage With Dock. Walk to Road America

Do you like tranquil, peaceful and serene? Don’t miss out on our lake front house. Huge windows with lake views and lots of natural light. Walking distance to Road America. Relax by our outdoor fire pit. Fish or kayak off or dock or swim within 900 ft of the driveway. Enjoy our game room with Pac-man video console or play corn hole. Quiet and relaxing but minutes to the Kettle trails and Historic downtown Elkhart Lake.

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.

Cozy cabin w/ hot tub & BBQ grill

Welcome to your peaceful forest cabin near Lake Michigan - a cozy retreat tucked among trees and designed for relaxed group stays year-round. - Sleeps 10 | 4 bedrooms | 7 beds | 3 baths - Private hot tub (Nov-Apr) & outdoor fire pit - 3 decks + large three-season room - Kitchen, dining table & board games - 50 inch HDTV, Wifi, record player - Lake access, shared beach access & beach essentials