Holiday rentals with a patio in Plymouth

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

Cedar Soaking Hot Tub ~King BED ~No Cleaning Fee

🤩No Cleaning Fees added to end cost! 🌟Licensed by County. Welcome to Sandy Bay LakeHouse. 🌊 Listen to the waves of Lake MI~2 blocks away~in this newly built 2BR/1BA home (2023). The home is conveniently located within walking distance of Neshotah Beach/Park (2 blocks). Ice Age Trail access directly across street ~ Walsh Field across street. Outdoor Cedar Soaking Hot Tub, along with Lava Firetop table & quality outdoor furniture ensures your time at Sandy Bay Lake House is relaxing & memorable

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!

Castle Vineyard | Luxe Spa • Golf Sim • Theater

Stay at one of the most Wishlisted Airbnbs in the world. Featured in Men’s Journal 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

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.

Downtown Plymouth, WI Second Floor 2 Bed Apartment

Second floor apt. with two single bedrooms, a queen bed and a full bed in the other. Full bath, kitchen, living room, outdoor smoke deck, long driveway for parking (first 3 feet of the driveway are steep). Enjoy a short walk to many shops and restaurants or check out the wall murals in the Cheese Capital of the World! You don’t have to travel too far for excitement Road America (4.5 mi), Plymouth Dirt Track (1.1 mi), Whistling Straits Golf Course (20.5 mi) Kettle Moraine nature trails 20.4 mi

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.

Barndominium with Goats, Hot Tub, Forest & River

The Cloverland Barndominium is a thoughtfully renovated 100-year-old barn sitting on 5+ private acres of forest to explore next to a river. You'll share the land with friendly goats and chickens that you can watch from right outside your window! Outside you'll enjoy walking the trails, feeding the animals, taking the canoe down the river, making a fire in the fire pit, and exploring the forest. Escape the busy world and reset!

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!