Holiday rentals with a patio in Elkhart Lake

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

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.

Picturesque Port Washington-HomePort LLC

The apartment is the lower level of our home in picturesque Port Washington. Quiet neighborhood, close to parks and close to bike path. There is 1 parking space and a separate entrance in the back of the house. There is a double futon in living area, bedroom has a queen size bed and newly renovated bathroom with a large shower. We are located 2 miles west of downtown Port which has many quaint shops, restaurants and a marina offering many opportunities for outdoor recreation and relaxation.

Modern Lower Apt - One block to the Lake

Part 1 of 2 Amazing AirBnB apartments in this ideally located duplex. *Disclaimer - this apartment offers a true lower level living experience. You may notice some noise, including foot traffic, from your amazing upstairs Airbnb neighbors. But.. with all the great restaurants, golf, fishing, and the beach nearby you won’t even have the time to hear it! Located only 1 block from the beach on Lake Michigan - you’ll find relaxation and a great time here at the heart of Sheboygan’s Shoreline.

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!

State Park Getaway with Hot Tub & Arcade

This fully remodeled A-Frame is walking distance to hiking trails and has views of Lake Winnebago. The outdoor enthusiast will find endless opportunities for adventure (canoeing, hiking, fishing, snowshoeing, biking) at High Cliff State Park. Take in the forest views from your private backyard with a large hot tub, fire pit, or relax on the private deck with stunning views of Lake Winnebago. Create memories with the private hot tub, giant chess board, arcade, and huge selection of games.

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 Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

Adorable bungalow in historic Sheboygan Falls,WI

Cute bungalow located on a quiet cul-de-sac with a relaxing pond and a large fenced in yard. Centrally located within 20 minutes of Elkhart Lake, Whistling Straits and the shores of Lake Michigan. Also, it is a quick walk to quaint Downtown Sheboygan Falls where there is plenty of shopping, dining, parks, the Sheboygan River, and waterfalls. I also run a company called Rescue Dog Properties and will be donating 5% of all bookings to Paws Up Pet Rescue based in Sheboygan.

Wander Back Inn to Elkhart Lake

This gorgeous, new home is the perfect choice for your trip to Elkhart. Mere minutes away from famous local attractions - Road America, Elkhart Lake, the Ostoff Resort, and more - you couldn’t get a better location. Or spend the day in and enjoy a BBQ on the patio, foosball, ping pong, shuffleboard, and more! With 4 spacious bedrooms, 3 full baths, and large social areas, this house has more than enough space for the whole group. Check In 4pm. Check Out 10 am.

Fall Retreat • Firepit • Gazebo • Near Lake & Zoo

🍂 Cozy 3BR across from Menominee Park & Lake Winnebago! Enjoy fall walks to the beach, zoo, and lakeside trail—all just steps from the house. A few minutes’ drive brings you to downtown Oshkosh with restaurants, shops, and nightlife. Sleeps 8 with a new upstairs king suite & Roku TV, plus an upstairs lounge & basement bar. 🔥 Unwind under the gazebo with a gas firepit—perfect for cooler evenings. Includes driveway parking and self check-in for a smooth stay.