Vacation rentals in Sheboygan

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Top-rated vacation rentals in Sheboygan

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.
Home in Sheboygan
4.98 out of 5 average rating, 103 reviews

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

Top guest favorite
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.
Home in Sheboygan
4.97 out of 5 average rating, 119 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.

Top guest favorite
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
4.97 out of 5 average rating, 141 reviews

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

Guest favorite
A leather sectional sofa is positioned beside a round coffee table, set on a textured area rug. A vintage surfboard is displayed above the couch, complementing the decor. A chair and lamp provide additional seating, while a small dresser holds a decorative lamp, enhancing the cozy ambiance.
Apartment in Downtown Sheboygan
4.91 out of 5 average rating, 149 reviews

Sheboygan Surf House - North Point

This super spacious studio apartment is the largest of our 3 spaces, located above Wisconsin's first Surf shop which is located in the heart of Sheboygan's Downtown District. Located directly next to bars , shopping and widely known restaurants like Tratoria Stephanos, Feild to Fork and IL Ritrovo, make walking everywhere easy. Whether you are here for beach days, a little get away or a wedding we are close to it all. Blue Harbor Resort, River front and the shores of Lake Michigan are close.

Top guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances, including a large refrigerator and a gas range. Light granite countertops provide ample workspace, complemented by warm lighting from a stylish overhead fixture. The space is accentuated by a neutral-colored door leading to the entrance.
Apartment in Ellis Historic
4.98 out of 5 average rating, 125 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.

Top guest favorite
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.
Apartment in Sheboygan
4.9 out of 5 average rating, 109 reviews

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!*

Top guest favorite
A cozy backyard oasis is illuminated in evening light, featuring comfortable seating around a fire pit. An outdoor movie screen projects a vibrant image onto the adjacent wall, surrounded by lush landscaping and wooden fencing that enhances privacy.
Home in Sheboygan
4.95 out of 5 average rating, 136 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.

Top guest favorite
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.
Home in Sheboygan
4.98 out of 5 average rating, 224 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with King size bed. Secondary bedroom has 2 twin beds. 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!

Guest favorite
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.
Apartment in Ellis Historic
4.93 out of 5 average rating, 533 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.

Guest favorite
A welcoming living area is highlighted by a warm orange couch with blue accent pillows. A modern lamp with a red base stands beside it on a side table. A framed painting adds character, while a plant is visible through a doorway leading to another room.
Home in Sheboygan
4.94 out of 5 average rating, 125 reviews

King Bed Near Lake w/ Fire Pit & Pack N Play

Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

Top guest favorite
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.
Home in Sheboygan
4.94 out of 5 average rating, 207 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.

Guest favorite
A spacious living room is equipped with a comfortable sofa and two armchairs. A TV screen is positioned adjacent to an original fireplace, which now houses an electric device. Natural light enters through a window, and a decorative area rug enhances the room's charm.
Apartment in Ellis Historic
4.86 out of 5 average rating, 111 reviews

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

Popular amenities for Sheboygan vacation rentals

When is the best time to visit Sheboygan?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,066 ZARR2,152 ZARR2,221 ZARR2,393 ZARR2,531 ZARR3,134 ZARR3,427 ZARR3,427 ZARR2,703 ZARR2,652 ZARR2,256 ZARR2,273 ZAR
Avg. temp-8°C-6°C0°C7°C14°C19°C21°C20°C16°C9°C2°C-4°C

Frequently Asked Questions

  • Where should I stay in Sheboygan?

    Make yourself at home in Sheboygan by choosing from our most frequently booked neighborhoods. We have over 220 vacation rentals in King Park, over 220 vacation rentals in Business Drive North, and over 220 vacation rentals in James Madison.

  • Are there vacation rentals with a dedicated workspace in Sheboygan?

    Yes! Work meets play with ease at over 140 vacation rentals in Sheboygan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Sheboygan?

    Four-legged friends are welcome in Sheboygan. Choose from more than 80 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Sheboygan?

    Experience the best of Sheboygan with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Sheboygan have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Sheboygan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Sheboygan have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Sheboygan. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Sheboygan have self check-in?

    Absolutely! We offer over 10 apartment rentals with self check-in in Sheboygan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Sheboygan have wifi?

    Absolutely! We offer over 150 house rentals with wifi in Sheboygan. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Sheboygan?

    Sheboygan has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Sheboygan?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with self check-in, over 70 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Sheboygan

  • Total vacation rentals

    Explore 280 vacation rentals in Sheboygan

  • Nightly prices starting at

    Sheboygan vacation rentals start at R689 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 13,630 verified reviews to help you choose

  • Family-friendly vacation rentals

    220 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    280 of Sheboygan vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Sheboygan rentals

  • 4.9 Average rating

    Sheboygan stays are highly rated by guests—averaging 4.9 out of 5!

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