Vacation rentals in Sheboygan

4.91 out of 5 average rating, 344 reviews

A serene lakeshore scene is captured at sunset, with the sun dipping below the horizon, casting warm hues across the sky. Gentle waves are visible in the foreground, while smooth stones line the water's edge.

Guesthouse in Oostburg

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

The two-story home features a charming yellow exterior with white trim and a red metal roof. Flower baskets hang from the porch, which is framed by neatly manicured bushes and vibrant landscaping. A sidewalk leads to the entrance, enhancing accessibility.

4.81 out of 5 average rating, 275 reviews

Home Away From Home-One Block From Lake Michigan!

Centrally located and pet-friendly! Walk to the beach, parks, and downtown Sheboygan. This spacious two-story home perfect for groups features flexible bedroom setups, a fully equipped kitchen, dining room, fenced backyard, and parking for up to 4 vehicles. Base pricing is competitive for small groups $15/guest per night for more than 2 guests. Close to golf courses, many family spots, restaurants, and 16 miles from Road America. Watch “Sheboygan Airbnb” on YouTube for a full walkthrough!

5 out of 5 average rating, 127 reviews

A wooden table displays a variety of items: an open book, a lime, a glass filled with dark liquid, and a bottle of rum beside a vintage Coca-Cola. A bouquet of vibrant flowers sits neatly in the background, with light filtering through a window.

Apartment in Kohler

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

A sunlit parlor features a rich hardwood floor, soft area rug, and a baby grand piano positioned near large windows. A vintage chandelier hangs above a circular table surrounded by elegant seating, complementing a framed artwork on the wall.

4.97 out of 5 average rating, 215 reviews

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

A hot tub, illuminated with soft blue lights, features cascading water and inviting seating. Adjacent, a traditional sauna with wood paneling provides a relaxing retreat. Decorative cushions accent modern chairs nearby, enhancing the tranquil space.

4.98 out of 5 average rating, 203 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully landscaped and decorated boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with Stearns and Foster King size bed. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

4.72 out of 5 average rating, 113 reviews

An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

4.98 out of 5 average rating, 153 reviews

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 exterior of a charming house is depicted, showcasing a welcoming front porch with steps leading up. The porch features a small seating area and decorative plants, while lush green grass frames the path, adding to the inviting ambiance.

4.96 out of 5 average rating, 193 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

A comfortable living area features a sectional sofa in a soft grey hue, a rustic wooden coffee table, and natural light streaming through large windows. Unique décor includes a vintage style chair and a wall-mounted shelf with plants and books.

4.93 out of 5 average rating, 504 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

4.94 out of 5 average rating, 200 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.

A compact kitchen area showcases modern cabinetry and essential appliances, including a refrigerator and a stove. A small counter with two stools provides a space for dining or working, accented by natural light filtering through a window. Decorative elements enhance the inviting atmosphere.

4.84 out of 5 average rating, 227 reviews

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

4.83 out of 5 average rating, 463 reviews

A view of the serene shoreline along Lake Michigan is presented, framed by lush greenery. A blue railing leads down toward the beach, where sand and water are visible, inviting outdoor activities. The sky is overcast, creating a calm atmosphere.

Guesthouse in Sheboygan

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

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Popular amenities for Sheboygan vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Sheboygan

An inviting living area features a dark leather couch and chairs arranged around a coffee table, with a large flat-screen TV mounted on the wall. A dining table with several black chairs sits nearby, and a door leads to an outside area. Soft lighting enhances the space.

5 out of 5 average rating, 16 reviews

Geele Getaway 2 BD Comfortable Stay.

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

4.97 out of 5 average rating, 93 reviews

House Near the Lake

A modern living area is highlighted by a sleek fireplace integrated into a stylish wall. Large windows provide natural light, complemented by comfortable seating and decorative elements. A wooden coffee table is centered on a soft rug, creating an inviting space for relaxation.

5 out of 5 average rating, 16 reviews

Beachside Beautifully Renovated Historic Home

4.83 out of 5 average rating, 6 reviews

The exterior of the beachfront condo showcases a welcoming entrance with two main doors framed by large windows. Thoughtfully landscaped gardens and a manicured pathway lead towards lush green space, offering views of rolling hills and nearby beach access.

Villa in Sheboygan

Wandering Waves - Lakefront | Stay on the beach!

Place to stay in Elkhart Lake

A tree-lined pathway leads to a cozy cottage, framed by colorful fall foliage. Orange pumpkins are placed near vibrant purple flowers, enhancing the seasonal charm. The yard is spacious, surrounded by mature trees, providing a serene and inviting atmosphere.

4.97 out of 5 average rating, 232 reviews

Cottage @ Schoolhouse*Firepit*Petfriendly

A cozy living room is featured, with a dark sofa, light-colored chairs, and a round pouf. A woven pendant light hangs above, illuminating textured wall art. Natural light filters through multiple windows, highlighting a striped area rug laid on the wooden floor.

4.89 out of 5 average rating, 100 reviews

The Beach | Sheboygan 2Br/1 Ba

A comfortable seating area is showcased with a wood-framed sofa and armchairs, adorned with decorative pillows. A round coffee table sits in the center, while floor lamps provide soft lighting. A large mirror reflects the space, enhancing the bright and airy atmosphere.

5 out of 5 average rating, 6 reviews

Cozy Cottage just steps from Lake MI

A two-story brick home is set against a clear blue sky, featuring a well-maintained front yard with lush green grass. The entrance is framed by neatly trimmed shrubs, with an inviting porch and adjacent driveway leading to a detached garage.