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!

Grammy’s house in a quiet and convenient location

Your family will be close to everything when you stay at this centrally-located place. The home will provide you a very comfortable and relaxing place to stay while you enjoy everything Sheboygan has. We will keep on hand all those little things you may need so that you don't have to travel with them if you don't want. The kitchen is stocked with items needed to cook if you are tired of fast food drive thru. All the comforts of home, away from home. We thank all of our guests for their feedback.

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.

Quaint Blast from the Past - walk to lake/8th st

Renovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our "Blast from the Past" as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!

Stay in a Real Castle on a Vineyard

Stay at one of the most Wishlisted Airbnbs in the world — a castle on a vineyard. Featured in Men’s Journal and on the cover of Haven magazine, The Castle Vineyard is a 20-acre estate built for unforgettable stays. 🍇 Vineyard estate with spa, sauna & wildlife views 🎬 Theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen with Viking appliances 🔥 Fire pit, patio & hot tub 🏰 “Felt like royalty… every detail was magical.” 🎉 Entire estate is yours. Ask about our exclusive Tasting Room.

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

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.

The Finish Line

Our cozy refurbished Cape Cod getaway is just steps from the downtown action, but offers a quiet respite at the end of the day. Enjoy the comfortable beds, fully appointed kitchen, fireplace, BBQ grill, onsite parking, outdoor patio, and big back yard. Walk to downtown restaurants and attractions, the Osthoff Resort, the Throttlestop, and beautiful Elkhart Lake, all just blocks away. About one hour from Lambeau Field, Milwaukee, or EAA. The Finish Line is your home away from home.

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.

Unmatched Location, Views, & Style. Welcome Home!

Be in the heart of the all the action, The lake, river, marina, boardwalk, and downtown are mere steps from this newly constructed gem. The blue house on the hill is perched where the mouth of the Sheboygan River meets Lake Michigan. Take in the view mornings, evenings, and in between from the stunning kitchen, living room or sailboat shaped front porch. Entertain openly and relax at this one of a kind property. No stairs required. Ramp for easy age friendly access.