This guest house is situated on the south side of Sheboygan, just three blocks from Lake Michigan and a short drive from Kings Park and South Beach, offering a peaceful retreat close to the city's attractions. The property has consistently received excellent ratings for its cleanliness, location, and user experience. The guest house features a comfortable living room and dining room, perfect for relaxing with family and friends, and can accommodate up to four guests. Amenities include a fully equipped kitchen, a spacious garden with a fire pit, and a washer and dryer, ensuring a comfortable and convenient stay.
9.8 12 reviews
Sheboygan, WI
04/07 – 06/07
NZ$687/nighttotal: NZ$1374 (2 )
Logan Ave Holiday House - Upper
2 2
apartment , Sheboygan
This apartment is situated in a residential area just 1.5km from Sheboygan's downtown and a short walk from the lakefront, offering a peaceful setting with easy access to attractions. Guests consistently rate the property excellent for its cleanliness, location and overall experience. The apartment has two bedrooms, each with a queen bed, and a queen sofa bed in the living room, comfortably accommodating up to six guests. The apartment offers modern amenities such as a fully equipped kitchen, a washer and dryer, central heating and air conditioning, and a shared backyard, making it a great choice for families or groups looking for a relaxing and comfortable stay.
10 7 reviews
Sheboygan, WI
29/06 – 02/07
NZ$438/nighttotal: NZ$1314 (3 )
Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit
3 3
apartment , Sheboygan
This three-bedroom Sheboygan holiday home is situated near Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park. Offering a mid-century modern design, this self-catering property sleeps six, includes a fully equipped kitchen with basic staples, a fenced backyard, a games room with a foosball table, and amenities such as shampoo, conditioner, and dishwasher tablets.
Sheboygan, WI
27/06 – 04/07
NZ$3240/nighttotal: NZ$22680 (7 )
Private, 4-bedroom, 2.5-bath Near Kohler Golf & Walking Distance To Winery!
4 2
apartment , Kohler
This four-bedroom property is situated just north of Kohler, less than 24 kilometres from Whistling Straits and within walking distance of Blind Horse Winery. It's located on a quiet street, offering a peaceful retreat after exploring the area's attractions. The spacious apartment covers 223 square metres and comfortably accommodates up to 10 guests. It includes a fully equipped kitchen, a private garden, a terrace, and a three-car garage with space for a gym, ensuring a comfortable and enjoyable stay.
10 12 reviews
Sheboygan, WI
27/06 – 04/07
NZ$2707/nighttotal: NZ$18949 (7 )
Private Log Home Retreat On 15 Acres With A Pond!
6 2
apartment , Kohler
This executive retreat in Kohler, Wisconsin, is situated on 24 hectares of private land, a 15-minute drive (approx. 24km) from Road America race track, 2 minutes from Kohler restaurants, and 5 minutes (approx. 8km) from Sheboygan and Lake Michigan's beaches. This six-bedroom, five-bathroom property sleeps ten guests and boasts a fully equipped gourmet kitchen, expansive deck, private fishing pond, and abundant recreational amenities including a pool table, ping pong, pickleball court, Peloton exercise bike, driving net, putting green, cornhole, and outdoor fire pit.
9.9 22 reviews
Sheboygan, WI
18/09 – 25/09
NZ$193/nighttotal: NZ$1351 (7 )
Executive Remodel, Fenced-in For Pets, Game Room!
1 4
apartment , Sheboygan
This Sheboygan duplex apartment offers a completely private first floor and lower level, with its precise location providing easy walking access to various Sheboygan attractions, though specific distances aren't detailed. The self-catering property sleeps up to six guests (four in beds, two on sofas), boasting a dedicated pet lounge, extensive games room, fully equipped kitchen, private parking, laundry facilities, and shared access to a backyard with a fire pit.
10 1 review
Sheboygan, WI
03/07 – 06/07
NZ$1419/nighttotal: NZ$4257 (3 )
Beautiful 3br Home Near Lake Mi
3 2
apartment , Sheboygan
This three-bedroom, two-bathroom flat is located in a quiet Sheboygan neighbourhood, just 100 metres from Lake Michigan and within a five-kilometre drive of Deland Park, North Beach, and downtown Sheboygan's shops and restaurants. This family-friendly apartment accommodates up to seven guests and offers a fully equipped kitchen, air conditioning, a private driveway, free street parking, and a dedicated workspace with Wi-Fi, with a crib also available for infants.
9.9 116 reviews
Sheboygan, WI
10/08 – 13/08
NZ$546/nighttotal: NZ$1638 (3 )
Janelle's Dockside Condo
2 2
apartment , Sheboygan
This two-bedroom apartment is located in Sheboygan's South Pier District, just a short walk from the boardwalk and its attractions, offering easy access to the area's charm and attractions. It has received excellent ratings for location, cleanliness, and overall guest experience. The property has two bathrooms and can accommodate up to four guests. The apartment comes equipped with modern amenities, including a fully equipped kitchen, air conditioning, and a private deck overlooking Lake Michigan. Guests can enjoy the nautical theme, explore the nearby golf courses, or simply relax and take in the scenic views.
9.2 5 reviews
Sheboygan, WI
27/06 – 04/07
NZ$303/nighttotal: NZ$2121 (7 )
Apartment Centrally Located
2 2
apartment , Howards Grove
This two-bedroom flat in Plymouth is situated near Esch Library and is a 27-kilometre drive from Lake Michigan, offering convenient access to local resources and outdoor pursuits. This accommodation provides air conditioning, Wi-Fi, and parking for up to four guests, with nearby golf courses and fairgrounds catering to leisure activities.
10 72 reviews
Sheboygan, WI
29/06 – 02/07
NZ$491/nighttotal: NZ$1473 (3 )
Character Filled 3 Bedroom Carriage House
3 3
farm , Sheboygan
This charming farm stay, located directly behind the historic Reiss Mansion in Sheboygan, offers a peaceful retreat just a short distance from the city centre. The property has received excellent ratings for its cleanliness, location, and user experience. The renovated carriage house provides a unique and comfortable accommodation for up to six guests, featuring three bedrooms, one bathroom, and a fully equipped kitchen. Amenities include a king-size bed in the master bedroom, a queen-size adjustable bed and twin beds in the other rooms, a dining room, a washer and dryer, and free parking.
9.8 10 reviews
Sheboygan, WI
18/09 – 25/09
NZ$258/nighttotal: NZ$1806 (7 )
Urban Lake Condo In Sheboygan's Historic Ellis District
2 4
apartment , Sheboygan
This Sheboygan apartment rental is situated in the historic Ellis District, less than 1.6km from the John Michael Kohler Arts Centre and Blue Harbor Resort, and approximately 2.1km from Lake Michigan. The two-bedroom, one-bathroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a dishwasher, a Smart TV, and on-site parking; a children's playground is also available.
9.7 6 reviews
Sheboygan, WI
04/07 – 06/07
NZ$933/nighttotal: NZ$1866 (2 )
The Mcm, A Modern 3-bedroom Home With A Sparkle
3 2
apartment , Sheboygan
This apartment is located in Sheboygan, close to the city's cultural attractions and lively districts. It has received excellent ratings for cleanliness, location, and overall user experience. This spacious home sleeps up to six guests in its two bedrooms, with a queen-size bed in the master bedroom and full-size beds in the other rooms. The apartment offers a fully equipped kitchen, a bar, a garden, and parking, along with unique features like a hidden bookshelf door and a blend of modern and classic design elements.
Best family friendly Sheboygan, WI holiday rentals
Among the 274 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals
9.8 170 reviews
Sheboygan, WI
06/08 – 09/08
NZ$705/nighttotal: NZ$2115 (3 )
Spacious Home Near Lake Mi W/ Fire Pit
1 2
apartment , Sheboygan
This three-bedroom Sheboygan holiday home enjoys a convenient location near Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park. Sleeping six, the property offers a mid-century modern design, a fully equipped kitchen, a fenced garden with fruit bushes, a games room with a foosball table, smart TV, and self check-in; infant equipment is also provided.
10 2 reviews
Sheboygan, WI
10/08 – 13/08
NZ$393/nighttotal: NZ$1179 (3 )
Sheboygan Falls: Rochester Ranch 3bed/1bath
3 2
apartment , Sheboygan Falls
This family-friendly flat in Sheboygan Falls is a short walk from Rochester Park, offering a blend of mid-century character and modern updates. With three bedrooms, one bathroom, and a capacity for seven guests, this property includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden for your convenience.
9.9 83 reviews
Sheboygan, WI
20/09 – 25/09
NZ$391/nighttotal: NZ$1955 (5 )
Grammy’s House In A Quiet And Convenient Location
4 4
apartment , Sheboygan
This family-friendly four-bedroom house in central Sheboygan offers convenient access to local attractions and amenities. The property boasts a finished basement with office space, play area, and workout equipment, comfortably accommodating eight guests with a fully equipped kitchen and a newly enclosed toilet; a 10% discount is available for returning guests.
10 28 reviews
Sheboygan, WI
18/09 – 25/09
NZ$393/nighttotal: NZ$2751 (7 )
*New* Sleeps 8 & Spacious!
3 4
apartment , Sheboygan
This Sheboygan apartment, ideally situated a short 2.4km drive from the city centre and 3.2km from Lake Michigan's shore, offers easy access to Sheboygan's attractions. Sleeping up to eight guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen with Greenware cookware, Roku TVs in each bedroom and living area, free on-site laundry, and a private garden with parking; two well-behaved dogs are welcome.
Best Sheboygan, WI holiday rentals with a pool
Among the 274 accommodations in Sheboygan, WI, here are the 3 best rentals with a pool
10 1 review
Sheboygan, WI
27/06 – 04/07
NZ$3337/nighttotal: NZ$23359 (7 )
Your Own Private Resort For The Ryder Cup!
4 2
apartment , Sheboygan
This luxurious apartment in Sheboygan is situated near an environmental park with hiking trails and a river, offering a peaceful retreat just a short distance from the town centre. The property has received excellent ratings for its location, cleanliness, and overall user experience. The apartment has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. It features a range of amenities, including a swimming pool, jacuzzi, fitness centre, and a private outdoor space with fire tables and a gazebo, perfect for relaxing and entertaining.
10 8 reviews
Sheboygan, WI
10/08 – 13/08
NZ$4668/nighttotal: NZ$14004 (3 )
Baronwood Oasis | Pool + Arcade Mega Estate
7 2
apartment , Sheboygan
This luxurious 975-square-metre (10,500 sq ft) estate in Sheboygan, Wisconsin, is situated minutes from the renowned Whistling Straits golf course and Lake Michigan's shores. The seven-bedroom, seven-bathroom property sleeps up to 20 guests and boasts an indoor pool and spa, a private arcade, a gourmet kitchen, and concierge services, offering a truly exceptional Sheboygan holiday home experience.
Sheboygan, WI
10/08 – 13/08
NZ$1745/nighttotal: NZ$5235 (3 )
Luxury Pool Retreat-2 Acres-near Whistling Straits
1 2
apartment , Sheboygan
This spacious private retreat, ideal for a family getaway, is located just outside Sheboygan, offering convenient access to Whistling Straits (13 kilometres), Road America (32 kilometres), and Lake Michigan. This four-bedroom, four-bathroom holiday home accommodates up to 12 guests and features a large kitchen, multiple living areas, air conditioning, a fitness centre, and a seasonal heated outdoor swimming pool, set on 2 acres of private land.
Frequently asked questions about holiday rentals in Sheboygan, WI
What are the must-see sights in Sheboygan, Wisconsin, United States?
Sheboygan's a great place! For must-see sights, you've got the Sheboygan Maritime Museum, showcasing the city's rich history on the lake. The John Michael Kohler Arts Center is another highlight, with rotating exhibits and a stunning collection. And don't miss the beautiful Sheboygan Riverwalk, perfect for a stroll.
What are the best Airbnb and holiday rentals in Sheboygan, WI?
Are there any unique natural phenomena in Sheboygan, Wisconsin, United States?
Sheboygan's location on Lake Michigan provides stunning lakefront views and beaches. While not a unique natural phenomenon in the strictest sense, the lake's effect on the local climate and the beautiful shoreline are definitely worth experiencing. The wetlands around the city also offer interesting wildlife viewing opportunities.
What are the most popular Airbnbs in Sheboygan, WI?
What essentials should you bring to Sheboygan, Wisconsin, United States?
Pack comfortable walking shoes – you’ll be doing a lot of exploring! Sheboygan’s weather can be unpredictable, so layers are a good idea. Sunscreen and a hat are essential, especially during summer. And don't forget your swimwear if you plan on enjoying the beaches.
What are the best holiday rentals with a pool in Sheboygan, WI?
What famous events or festivals are happening in Sheboygan, Wisconsin, United States?
Sheboygan has several events throughout the year. The Bratwurst Days festival is a big one, celebrating the city's famous bratwurst. The Sheboygan County Fair is another popular annual event.
What are the best rentals for families and kids in Sheboygan, WI?
Where can you find the best restaurants serving local dishes in Sheboygan, Wisconsin, United States, and what are the must-try specialties?
You absolutely must try the local bratwurst! Many restaurants serve it, but look for places like the local pubs and eateries for an authentic experience. Sheboygan also has a great seafood scene due to its lakeside location, so explore the menus for fresh catches of the day.
What are the best rentals or Airbnbs with a jacuzzi in Sheboygan, WI?
What are some less-famous attractions in Sheboygan, Wisconsin, United States that are worth a visit?
The Sheboygan County Historical Museum offers a more in-depth look at local history than the Maritime Museum. The Evergreen Park offers beautiful green spaces and walking trails for a quiet retreat. The local farmers' markets are also a great way to experience local produce and crafts.
What are the best activities for engaging with locals and understanding their culture in Sheboygan, Wisconsin, United States?
Visiting the local farmers' markets is a great way to interact with residents. Attending community events like the Bratwurst Days festival will also give you a flavour of local culture. Simply striking up conversations with people in local businesses can lead to interesting interactions.
What unique natural landscapes and terrain features can travellers explore in Sheboygan, Wisconsin, United States?
Sheboygan's main natural feature is its stunning Lake Michigan shoreline, with its beaches and opportunities for watersports. The surrounding areas also feature wetlands and some rolling hills.
How many days are ideal for visiting Sheboygan, Wisconsin, United States, and what are some itinerary suggestions?
Two to three days is a good amount of time to explore Sheboygan at a relaxed pace. A possible itinerary could include: Day 1 – explore the downtown area, Sheboygan Riverwalk, and the Maritime Museum. Day 2 – visit the John Michael Kohler Arts Center and enjoy the beaches. Day 3 – explore the Evergreen Park and perhaps take a day trip to a nearby town.
Nearby regions
Best Sheboygan, WI holiday rentals with a balcony
10 16 reviews
Sheboygan, WI
18/09 – 25/09
NZ$263/nighttotal: NZ$1841 (7 )
Quaint Blast From The Past - Walk To Lake Michigan, Riverwalk And 8th St Shops!
2 4
apartment , Sheboygan
This Downtown Sheboygan apartment is situated less than 1.6km from Lake Michigan, the John Michael Kohler Arts Centre, and the Blue Harbor Resort & Conference Centre water park. This 102 square metre, two-bedroom, one-bathroom flat sleeps six guests and boasts a fully equipped kitchen, private balcony, swimming pool, spa, parking, and free Wi-Fi.
This four-bedroom beachfront apartment in Sheboygan's city centre, situated within the Blue Harbor Resort on Lake Michigan, offers easy access to attractions such as the Stefanie H. Weill Center and John Michael Kohler Arts Center. The 186-square-metre property sleeps ten guests, features three bathrooms (including a master suite with jacuzzi), a fully equipped kitchen, and a private balcony overlooking the courtyard and lake; nearby amenities include the Blue Harbor Resort & Conference Center Water Park and Above & Beyond Children's Museum.
Sheboygan, WI
06/08 – 09/08
NZ$667/nighttotal: NZ$2001 (3 )
The Beach Town Bungalow
2 2
apartment , Sheboygan
This two-bedroom flat in Sheboygan is a 10-minute walk from the Sheboygan County Historical Museum and a 5-minute drive from Lake Michigan. This apartment accommodates up to five guests and features air conditioning, a garden, a balcony, and on-site parking, with a fully equipped kitchen including a fridge and microwave oven, and in-unit internet access.
9.9 64 reviews
Sheboygan, WI
18/09 – 25/09
NZ$692/nighttotal: NZ$4844 (7 )
Family Home, 1 Block To Lake Michigan Beach!
3 4
house , Sheboygan
This house is located in Sheboygan, just a 1.6km walk from North Side Municipal Beach and a 1.6km drive from the Children's Museum. The house has received excellent ratings for its location, cleanliness, and user experience. This comfortable property spans 153 square metres and can accommodate up to 7 guests in its 3 bedrooms and 2 bathrooms. The house features a garden, a terrace, a fitness centre, and a spa, along with a fully equipped kitchen, air conditioning, and free Wi-Fi.
Best Sheboygan, WI holiday rentals with parking
9.8 53 reviews
Sheboygan, WI
20/09 – 25/09
NZ$384/nighttotal: NZ$1920 (5 )
The Perfect Location!
3 4
apartment , Sheboygan
This three-bedroom apartment is located in Sheboygan, just a short walk from both the historic downtown area and the beach, offering easy access to shops, restaurants, and the lakeside. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience. The property offers a spacious living area with a fully equipped kitchen, dining room, and three bedrooms, comfortably accommodating up to six guests. Amenities include a private garden, a front patio, free street parking, Wi-Fi, a washer and dryer, and a small yard, providing plenty of space for relaxation and outdoor activities.
10 6 reviews
Sheboygan, WI
29/06 – 02/07
NZ$702/nighttotal: NZ$2106 (3 )
Serene Home One Block From Lake Michigan
3 3
apartment , Sheboygan
This spacious three-bedroom, two-bathroom flat is located in Sheboygan's Ellis Historical District, just 100 metres from Lake Michigan and within walking distance of Deland Park, North Beach, and downtown amenities. Ideal for families, this property offers accommodation for six guests with a fully equipped kitchen, private parking, and is a 15-kilometre drive from Whistling Straits Golf Course and Kohler.
9.2 5 reviews
Sheboygan, WI
20/09 – 25/09
NZ$365/nighttotal: NZ$1825 (5 )
Charming 2-bedroom Condo With Wifi, Ac In Quaint Sheboygan
2 4
apartment , Sheboygan
This Sheboygan apartment, located in the Ellis Historical District, is close to Lake Michigan and North Side Municipal Beach, and within a short driving distance (approximately 8km) of the Blue Harbor Resort. The two-bedroom, one-bathroom flat sleeps four, offering queen beds, a fully equipped kitchen (including fridge and microwave), in-unit laundry, air conditioning, free Wi-Fi, and a hairdryer; nearby attractions include the Above & Beyond Children's Museum and Bookworm Gardens.
9.5 21 reviews
Sheboygan, WI
06/08 – 09/08
NZ$1848/nighttotal: NZ$5544 (3 )
Beach House In Sheboygan Near Downtown
1 2
apartment , Sheboygan
This Sheboygan beachfront property boasts unparalleled Lake Michigan access, situated directly on the public beach. The three-bedroom, two-bathroom house sleeps eight guests and features a fully equipped kitchen, ample parking, and multiple TVs, including one in each bedroom.