Vacation rentals in Sheboygan County

The exterior of a two-story brick duplex is displayed, featuring symmetrical windows and a welcoming front porch adorned with an American flag. A well-kept lawn surrounds the house, with blooming flowers and neat landscaping. Soft evening light enhances the home’s inviting presence.

4.98 out of 5 average rating, 169 reviews

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!

Superhost

A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

Apartment in Plymouth

4.64 out of 5 average rating, 311 reviews

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

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.

4.83 out of 5 average rating, 263 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, 123 reviews

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

4.95 out of 5 average rating, 176 reviews

An exterior view of the property features a wooden deck above with a railing, complemented by a staircase leading to the entrance. A paved area at the ground level includes plants and a grill, alongside a garage door and multiple windows of the main structure.

Home in Howards Grove

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

A sophisticated living area features rich wood paneling and a plush carpet. Two green upholstered chairs are positioned beside a round coffee table with decorative accents. A large mirror reflects the space, while a bookcase filled with various books and decor items adds character to the room.

4.97 out of 5 average rating, 211 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, 201 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!

Superhost

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

4.71 out of 5 average rating, 105 reviews

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.

5 out of 5 average rating, 143 reviews

The cabin's exterior features a modern design with a dark green facade and a sloped metal roof. Large windows reflect the surrounding greenery, while a gravel pathway leads to the entrance, framed by vibrant foliage and a landscaped yard.

Cabin in Cascade

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

A round wooden dining table is surrounded by four white chairs, set against a light grey carpet featuring a geometric pattern. A bowl of yellow fruit sits in the center of the table. Natural light streams in from the adjoining area, enhancing the neutral tones of the space.

4.98 out of 5 average rating, 148 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.

A sandy beach is set against a clear blue sky, with gentle waves lapping at the shore. Lush green grass borders the beach area, while several volleyball nets are positioned on the sand, indicating recreational opportunities nearby.

4.93 out of 5 average rating, 499 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.

Superhost

4.84 out of 5 average rating, 223 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

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Sheboygan County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Sheboygan County

A bright living space features high cathedral ceilings with exposed wooden beams and large windows providing natural light. Soft, plush seating is arranged around a circular coffee table, while a dining area is visible in the background. Contemporary art adorns the wall, enhancing the modern aesthetic.

5 out of 5 average rating, 8 reviews

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

JoseRating, 5 stars4 days ago

Best place ever, nice and clean, gaming area, pool table, definitely will stay again! Tyler was really nice 🤙

5 out of 5 average rating, 37 reviews

Unmatched Location, Views, & Style. Welcome Home!

CarlyRating, 5 stars5 days ago

This house is amazing!! Sparkly clean. It has beautiful natural daylight, and you can open all the windows to feel a nice breeze during the day. It’s well-stocked and has supplies for the beach, which was a major plus! Jill is very nice and was easy to get ahold of!

4.96 out of 5 average rating, 25 reviews

A sunroom is highlighted by large windows that provide views of the surrounding nature and river. A stone fireplace adds warmth to the space, complemented by a beige area rug on the wooden floor. Potted plants decorate the windowsills, enhancing the inviting atmosphere.

Home in Sheboygan Falls

“On The Water” the Sheboygan River Overlook

GraceRating, 5 stars1 day ago

The cottage is absolutely beautiful—quaint, peaceful, and right along the river which made it even prettier. Everything here was so thoughtfully prepared as it felt cozy and charming while also being fresh and comfortable. I couldn’t have asked for a better place to stay for a summer trip with my friends.

4.97 out of 5 average rating, 31 reviews

Condo in Sheboygan

Heavenly Condo in the Malibu of the Midwest

LisaRating, 5 stars3 months ago

Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.

A well-maintained backyard features lush green grass and a variety of trees and shrubs, creating a peaceful outdoor space. A wooden fence borders the area, and several garden features, like a bird feeder, enhance the natural setting. Sunlight filters through the leaves on a clear day.

5 out of 5 average rating, 88 reviews

Relaxing Sheboygan/Kohler Getaway

PatrickRating, 5 stars1 month ago

I'm not sure what I can add to all the other reviewers opinions. This is a great Airbnb and we've stayed in over 170. The hosts really put a lot of thought into making it perfect for guests. We came here to look for some special birds. Jaclyn's home is a birders paradise with six feeders in a wonderful backyard. If you look on a map, the home looks near the highway, but road sound is very minimal. The attached townhouse also did not create any audible sound. Please be respectful of them too.

4.93 out of 5 average rating, 90 reviews

An open-concept living space features a dining area with a round table and four chairs. Modern appliances are present in the kitchen, which includes white cabinetry and a large island. A cozy seating area includes a tan leather sofa and large windows allowing natural light.

Condo in Sheboygan

Janelle's Dockside Condo

KathleenRating, 5 stars2 weeks ago

Janelle’s place was spacious and sparkling clean. The location is great, right on the river and an easy walk to the lake. We would definitely stay again if we come back to Sheboygan.

5 out of 5 average rating, 36 reviews

The exterior view of the condo showcases a welcoming entrance with a private porch, adorned with white columns and railings. Lush landscaping enhances the property, and a subtle name sign identifies the villa, creating a charming and inviting atmosphere for guests.

Villa in Sheboygan

Lovely Lake Lookout - Cozy Condo Steps from Lake

StewardRating, 5 stars1 month ago

Danielle had a perfect place for us to stay long-term. The location is great: there are a variety of restaurants nearby, a wonderful coffee shop, the ice cream parlor opened for the season, Blue Harbour is right next door, and of course Lake Michigan. There is easy access to the beach area, including enough beach to enjoy. Our hosts were very friendly and responsive. If we had any questions or concerns, they responded immediately. When we needed to extend our stay, they worked with us to be able to do that. Fantastic hosts! The decor is warm and friendly. It definitely felt welcoming and comfortable. The only issue was with the drainage in the tubs (a bit slow), but they were addressing that, and hopefully it will be resolved. We would definitely recommend staying with Danielle!