Holiday Rentals in Sheboygan, WI

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Sheboygan, WI holiday rentals
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274 Holiday Rentals and Airbnb in Sheboygan, WI

Best family friendly Sheboygan, WI holiday rentals

Among the 274 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals

Spacious Home Near Lake Mi W/ Fire Pit - Sheboygan, WI
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.
Sheboygan Falls: Rochester Ranch 3bed/1bath - Sheboygan, WI
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.
Grammy’s House In A Quiet And Convenient Location - Sheboygan, WI
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.
*New* Sleeps 8 & Spacious! - Sheboygan, WI
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

Your Own Private Resort For The Ryder Cup! - Sheboygan, WI
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.
Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
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.
Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
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?

    Cozy Sheboygan Upper, Remodeled Home On Lake Michigan and Carriage House Sheboygan - Garage Parking Included are the most popular Airbnb and holiday rentals in Sheboygan, WI among travellers.

  • 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?

    Among the Airbnbs in Sheboygan, WI, Cozy Sheboygan Upper, Carriage House Sheboygan - Garage Parking Included and Remodeled Home On Lake Michigan are the most popular ones.

  • 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

Quaint Blast From The Past - Walk To Lake Michigan, Riverwalk And 8th St Shops! - Sheboygan, WI
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.
Perfect Paradise - Lakeview Condo W/ 7 Beds, Jacuzzi, And Balcony - Sheboygan, WI
9.6 28 reviews
Sheboygan, WI
18/09 – 25/09
NZ$777/nighttotal: NZ$5439 (7 )

Perfect Paradise - Lakeview Condo W/ 7 Beds, Jacuzzi, And Balcony

4 4
apartment , Sheboygan
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.
The Beach Town Bungalow - Sheboygan, WI
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.
Family Home, 1 Block To Lake Michigan Beach! - Sheboygan, WI
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

The Perfect Location! - Sheboygan, WI
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.
Serene Home One Block From Lake Michigan - Sheboygan, WI
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.
Charming 2-bedroom Condo With Wifi, Ac In Quaint Sheboygan - Sheboygan, WI
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.
Beach House In Sheboygan Near Downtown - Sheboygan, WI
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.
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