Holiday rentals with a washing machine and dryer in Sheboygan

4.99 out of 5 average rating, 296 reviews

Cabin in Elkhart Lake

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

4.97 out of 5 average rating, 110 reviews

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.

Apartment in Ellis Historic

4.97 out of 5 average rating, 113 reviews

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.

4.9 out of 5 average rating, 105 reviews

Apartment in Sheboygan

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

4.97 out of 5 average rating, 162 reviews

Lakeview Beach Bungalow - With outdoor Hot Tub!

Beautifully updated beach house just one block off of Lake Michigan. Enjoy the newly landscaped backyard with pergola and 6 person Hot Tub! Watch the sunrise and sunset from the second floor master balcony. Walk to the lake across the street and enjoy the wind surfers and beach. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated. First floor laundry. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach. .

4.94 out of 5 average rating, 107 reviews

Condo in South Pier

Janelle's Dockside Condo

GREAT LOCATION!! Built in late 2020. Come visit our luxury, "Nautical Themed" 2 bedroom condo in Sheboygan, WI located on the confluence of Lake Michigan and the Sheboygan River in the charming South Pier District. Relax on the deck with a beverage and watch the sailboats pass by. Stroll the boardwalk for fine dining, charter fishing, quaint boutiques or an afternoon ice cream. World class golfing at Black Wolf Run or Whistling Straights. Equipped with everything you need and more!

4.95 out of 5 average rating, 132 reviews

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.

Loft in Downtown Sheboygan

4.98 out of 5 average rating, 108 reviews

Spacious/stylish, 2br loft

Lots of space, ready-to-use kitchen w/cooking essentials, washer/dryer in unit, 1.5 baths, 2 queen, 2 twin, ready for family/friends. Stocked with home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking lot in rear but free nights/weekends. Wonderful, walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front (a bit further). Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

4.98 out of 5 average rating, 171 reviews

Apartment in Sheboygan

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.

4.94 out of 5 average rating, 204 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

4.98 out of 5 average rating, 281 reviews

Apartment in Waldo

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.