House holiday rentals in Sheboygan

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Top-rated house rentals in Sheboygan

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Guest favourite

A spacious living area features large windows framing a serene lake view, reflecting shimmering sunlight. A comfortable white sofa is positioned in front of the window, accompanied by a patterned armchair. Natural light fills the room, enhancing the coastal atmosphere.

Home in Oostburg

4.78 out of 5 average rating, 157 reviews

Newly Renovated Beach Front Home in Oostburg WI

If you are looking for a vacation get away, this is your place. If you enjoy the lake and the outdoors then this is where you want to find yourself. From our outdoor patio overlooking the lake, to the newly added outdoor shower, you can fully enjoy the outdoors. But wait, the outdoors isn’t all you have. You also have a newly renovated second floor addition that is a whole new area with plenty of seating overlooking the lake. There is a picture of the view included in the photos for the listing.

Guest favourite

The exterior of a charming Cape Cod home is depicted, featuring warm stone accents and a sloped roof. A small porch with railings is visible, alongside a single-car garage. Lush green grass and mature trees surround the property, creating a serene and natural setting.

Home in Sheboygan

4.79 out of 5 average rating, 33 reviews

Black River Retreat

Wow. An amazing home in an amazing location. Minutes from downtown Sheboygan, beaches at Kohler Andre & Lakeview parks, local golf courses & Road America. This beautiful Cape Cod has 3 bedrooms & a magnificent bath on the 1st floor. A giant suite upstairs w/ a private bath & even an indoor hammock. Wood-burning fireplace in the main living room & an eclectic study furnished in vintage furniture & a rare pinball. Stay in to relax, ponder, and read. Or make it your base camp for exploring the area

Guest favourite

A well-equipped kitchen features light-colored cabinetry, a countertop with two high-backed chairs, and a wall-mounted decorative piece that reads 'EAT.' Large windows allow natural light to brighten the space, while a refrigerator and an electric stove are visible.

Home in Sheboygan

4.92 out of 5 average rating, 25 reviews

Lake Breeze on 11

Sheboygan has lots to offer & our place is perfect for your homebase. The lakefront, Sunrise, End, & Vollrath park are just 7 blocks away. The historic downtown, area golf courses, Road America, & Kohler are all a short drive away. Come stay at this large, vibrant, comfy 2 bedroom home. Tastefully furnished with a bright, warm, beach like feel. The home is stocked with amenities to make your stay memorable, including an eclectic DVD’s, plenty of board games & record player. Come make memories!

Guest favourite

The exterior of the home features a charming two-story design with a gabled roof and a welcoming front entrance. Large windows allow natural light to fill the space. A small seating area is visible on the front patio, complemented by greenery and a neatly landscaped yard.

Home in Ellis Historic

4.92 out of 5 average rating, 48 reviews

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.