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Vacation rentals in Sheboygan

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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 $57 CAD per night before taxes and fees

  • Verified guest reviews

    Over 16,270 verified reviews to help you choose

  • Family-friendly vacation rentals

    230 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wifi availability

    270 of Sheboygan vacation rentals include wifi 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!

Top-rated vacation rentals in Sheboygan

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

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Top guest favourite
A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.
Apartment in Sheboygan

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!

FamilyValueBiking

4.99 out of 5 average rating, 283 reviews
Top guest favourite
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

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.

LocationFamilyGetting around

4.96 out of 5 average rating, 128 reviews
Top guest favourite
A serene view from the second-story balcony overlooks the sandy beach and expansive lake. Soft waves lap at the shore under a cloudy sky, with a faint rainbow visible in the distance, creating a tranquil atmosphere for relaxation.
Condo in Sheboygan

Amazing views beach condo for 12: 4 bdrm, 3 bath

Beach condo for 12 2,000+ s/f Safely located on the 2nd & 3rd floors of the building Walk out to the beach. Restaurants, shops, seasonal entertainment walkable to South Pier. 4 bedrooms. 2.75 baths. One bath with oversized jetted tub for 2. One bedroom great for kids: double bed + a bunk bed! Full kitchen. Breakfast bar seats 4. Dining table seats 6. Free in-unit washer/dryer 2 parking spots + free public overnight lot Guests do not have access to or use of Blue Harbor Resort waterpark

ValueFamilyHospitality

4.97 out of 5 average rating, 106 reviews
Top guest favourite
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

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.

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 176 reviews
Guest favourite
Castle in Cleveland

Castle on a vineyard with hot tub and theater

Stay at one of the most Wishlisted Airbnbs in the world — a castle on a vineyard. Featured in Men’s Journal and on the cover of Haven magazine, The Castle Vineyard is a 20-acre estate built for unforgettable stays. 🍇 Vineyard estate with spa, sauna & wildlife views 🎬 Theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen with Viking appliances 🔥 Fire pit, patio & hot tub 🏰 “Felt like royalty… every detail was magical.” 🎉 Entire estate is yours. Ask about our exclusive Tasting Room.

FamilyLocationOutdoor spaces

4.99 out of 5 average rating, 178 reviews
Top guest favourite
An inviting wellness space features a hot tub with gentle bubbles and soft green lighting. Adjacent, a wooden dry sauna awaits, surrounded by potted plants. Comfortable seating with decorative pillows is arranged nearby, creating a serene atmosphere for relaxation.
Home in Sheboygan

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/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. Let us impress you and help make it a memory.

LocationValueBreakfast

4.98 out of 5 average rating, 283 reviews
Top guest favourite
Home in Sheboygan

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.

LocationValueShared spaces

4.97 out of 5 average rating, 254 reviews
Guest favourite
A spacious living area features a dark leather sectional sofa with colorful throw pillows. A textured ottoman sits in front, while natural light streams through large windows, illuminating the warm brick wall and wooden furniture. A decorative coffee table holds books and a candle.
Loft in Sheboygan

Spacious/stylish, 2br loft

Beautiful, spacious loft in active downtown. Laundry, kitchen, 1.5 baths, 2 Qu, 2 Tw beds. Bakery & fitness studio on 1st floor (some a.m. noise). Stocked w/home essentials. Smart TVs, free WIFI. Pay-as-you-go parking in rear but free nights/weekends. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front near-by. Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

FamilyLocationNearby

4.95 out of 5 average rating, 138 reviews
Top guest favourite
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.
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.

FamilyLocationBackyard

4.98 out of 5 average rating, 225 reviews
Guest favourite
The image captures a scenic view from the deck, showcasing a lush green backyard leading to the shoreline of Lake Michigan. A fire pit is visible on the grass, and white planters frame the deck, while the sky displays a soft gray hue.
Home in Sheboygan

Stylish Getaway | Cozy Vibes | Perfect Girls Trip

Escape to a cozy, stylish retreat designed for relaxing weekends, girls trips, or family getaways. Start your morning with a sunrise and coffee on the patio looking out onto Lake Michigan, then spend the day exploring, and unwind at night around the firepit with a glass of wine. This home has everything you need for gathering and cooking together or cozying up to the fireplace and playing board games. A short walk to town, close to golf, breweries, winery, and a state park.

LocationValueBeach

4.94 out of 5 average rating, 229 reviews
Top guest favourite
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 Sheboygan

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.

LocationValueOutdoor spaces

4.93 out of 5 average rating, 607 reviews
Guest favourite
A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating includes a sectional sofa and two armchairs, arranged around a stylish fireplace with intricate tile work. Light-colored curtains complement the modern decor.
Home in Sheboygan

The Suncatcher -Steps from Lake - Fenced Yard

Welcome to the Suncatcher. Our cozy and bright Midwest retreat just a block away from Lake Michigan . Step into our lovingly remodeled 1930's home where modern comfort meets timeless charm. As you enter you will be greeted by the inviting warmth of exposed brick walls and abundance of natural light that fill every corner. With three bedrooms and two bathrooms, our spacious retreat is perfect for families, friends, or golf enthusiasts seeking a relaxing getaway.

FamilyValueBathroom

4.97 out of 5 average rating, 106 reviews

Popular amenities for Sheboygan vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Sheboygan's top sights

Kohler-Andrae State Park

143 locals recommend

Bookworm Gardens

86 locals recommend

Blackwolf Run Golf Course

80 locals recommend

Deland Park

45 locals recommend

Blue Harbor Resort

35 locals recommend

Evergreen Park

12 locals recommend

Other great vacation rentals in Sheboygan

Top guest favourite
A well-lit bedroom features a queen-size bed with a patterned blue and white duvet, complemented by neatly arranged towels. A nightstand with a bedside lamp stands beside the bed, and natural light enters through a window dressed with blue curtains.
Condo in Sheboygan

Ellis District Urban Lake Condo

LocationValueBeach

4.94 out of 5 average rating, 85 reviews
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 Sheboygan

The perfect location!

LocationFamilyHospitality

4.9 out of 5 average rating, 69 reviews
Top guest favourite
A spacious living area features a comfortable navy blue sectional sofa, complemented by two cushioned chairs. A wooden coffee table sits at the center, while artwork adorns the walls. Soft lighting from multiple chandeliers creates a welcoming environment.
Home in Sheboygan

Sheboygan's Great Lakes House

LocationFamilyNearby

4.99 out of 5 average rating, 94 reviews
Top guest favourite
Home in Sheboygan

Luxury Villa on Lake Michigan!

LocationFamilyAmenities

5.0 out of 5 average rating, 27 reviews
Top guest favourite
Condo in Sheboygan

Riverfront Fall Getaway Near Lake Michigan

FamilyLocationNearby

5.0 out of 5 average rating, 22 reviews
Guest favourite
The waterfront view captures the inviting exterior of the condo building with boats docked along the river. A spacious patio area is visible, offering access to the water. The surrounding landscape features manicured lawns and walkways, enhancing the serene riverfront setting.
Condo in Sheboygan

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

LocationFamilyWalkability

4.9 out of 5 average rating, 83 reviews
Top guest favourite
Home in Sheboygan

Eve’s Place by beach 2 kings 1 queen + Pack’n Play

FamilyLocationCleanliness

5.0 out of 5 average rating, 33 reviews
Top guest favourite
Apartment in Sheboygan

Riverfront Loft - Fantastic location

FamilyLocationCleanliness

5.0 out of 5 average rating, 43 reviews

When is the best time to visit Sheboygan?

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Avg. price$184 CAD$191 CAD$191 CAD$214 CAD$251 CAD$286 CAD$294 CAD$284 CAD$217 CAD$214 CAD$203 CAD$196 CAD
Avg. temp-8 °C-6 °C0 °C7 °C14 °C19 °C21 °C20 °C16 °C9 °C2 °C-4 °C

Frequently Asked Questions

  • What are the best places to stay in Sheboygan?

    Many guests look for stays near the lakefront, South Pier District, or around downtown for easy access to dining and cultural activities. Neighborhoods near parks and the marina are also frequently suggested for a relaxing atmosphere.

  • What are the best things to do in Sheboygan with kids?

    Children often enjoy exploring Bookworm Gardens, playing at Above & Beyond Children's Museum, and visiting the beach at Deland Park. Summer paddleboat rentals and splash pads are also popular family activities near the lakeshore.

  • What are some of the best things to do in Sheboygan?

    Enjoy the sandy shore at North Beach, experience interactive art at the John Michael Kohler Arts Center, or paddle along the Sheboygan River. The South Pier District has lively dining, shopping, and harbor walks for a relaxed outing.

  • How is the weather in Sheboygan?

    Sheboygan has cold winters with daytime highs near 11–31°F (-12 to -1°C) and snow, while summers are mild, often around 60–81°F (16–27°C) with lake breezes and moderate rain. Spring and fall bring varying temperatures, so a jacket is usually useful.

  • When is the best time to visit Sheboygan?

    Late spring through early fall is often recommended for mild temperatures and outdoor activities, with summer bringing festivals and lakefront events. For those who enjoy snow sports or quieter streets, winter reveals a different pace along the lake.

  • What are the best places to visit in Sheboygan?

    Explore Bookworm Gardens, a whimsical botanical space, and stroll the scenic boardwalk at South Pier District. The John Michael Kohler Arts Center and Deland Park are also frequently suggested for art lovers and outdoor enthusiasts.

  • What are some hiking trails in Sheboygan?

    Explore forested trails at Maywood Environmental Park or walk the Blue Harbor Boardwalk along the waterfront. Kohler-Andrae State Park, just outside Sheboygan, has sandy dune trails and boardwalks through woodlands and marshes.

  • What are some family activities we can do in Sheboygan?

    Families often visit Bookworm Gardens and enjoy hands-on exhibits at Above & Beyond Children's Museum. North Beach and Deland Park are popular for lakeside picnics, while Sheboygan Quarry has summer water activities for various ages.

  • What are some of the best day trip ideas from Sheboygan?

    Explore state parks along the Lake Michigan shoreline, stroll through the historic downtown of nearby towns, or try rural cheese-tasting experiences. Small lighthouses, farm markets, and outdoor nature trails are often recommended for a relaxed outing.

  • Are there any pet friendly accommodations available in Sheboygan?

    Many vacation rentals and local stays in Sheboygan welcome pets, especially near the lakefront and parks. Outdoor patios and walking paths around South Pier District and residential neighborhoods make it easier to include your companion.

  • What are some local tips for visiting Sheboygan?

    Layer clothing throughout the year, as Lake Michigan influences the weather with cool breezes even in summer. Locals often explore the lakefront, sample bratwurst from neighborhood spots, and check the calendar for festivals or markets around downtown.

  • What is Sheboygan known for?

    Sheboygan is known for its sandy Lake Michigan shoreline, locally rooted surf culture, and longstanding bratwurst traditions. The city also has a strong reputation for arts programming and public sculpture installations.

  • What are the best hidden gems to explore in Sheboygan?

    Explore the restored trails at Maywood Environmental Park for a quieter experience and discover eclectic art installations on less-traveled city streets. The local farmers market and intimate coffee shops around downtown are also often suggested.

  • What are the best foods to try in Sheboygan?

    Sheboygan has bratwurst served on hard rolls as a signature dish, and cheese curds reflect the region’s dairy traditions. Visitors also often enjoy dishes made from fresh Lake Michigan fish, and Wisconsin treats like kringle are available in neighboring cities.

  • What should I bring for a trip to Sheboygan?

    Pack layers all year, since Lake Michigan breezes can be cool even in summer, and bring a jacket or raincoat for changing weather. Walking shoes, swimwear, and a camera are also helpful for exploring the lakefront and parks.

  • What is the nightlife in Sheboygan like?

    Nightlife in Sheboygan centers around downtown and the South Pier District, with relaxed pubs, small music venues, and local breweries. Many spaces host live bands, trivia nights, or open mic events for an approachable evening out.

  • What are the most popular events or festivals in Sheboygan?

    Sheboygan has summer events like Bratwurst Days, outdoor concerts, and art fairs that are frequently suggested by locals and visitors. Community gatherings often happen during warmer months, bringing music, food, and craft activities to the lakefront and city parks.

  • Are there family friendly vacation rentals in Sheboygan?

    Sheboygan has many vacation rentals suitable for families, especially near the lakefront, South Pier District, and residential neighborhoods around parks. Listings often highlight amenities like extra bedrooms, kitchens, and easy access to outdoor spaces.

Destinations to explore