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

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub - Sheboygan, WI
9.8 52 reviews
Sheboygan, WI
10/08 – 13/08
NZ$1268/nighttotal: NZ$3804 (3 )

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

1 2
apartment , Sheboygan
Sheboygan Chalet, a four-bedroom lodge in Sheboygan's Black River neighbourhood, is situated two blocks from Lake Michigan and a short walk from Majerle's Supper Club, ten minutes' drive from Sheboygan's town centre.
This self-catering holiday home sleeps up to 13 guests and boasts a chef's kitchen, games room with PS5 and arcade machines, hot tub, infrared sauna, and two expansive decks, all within easy reach of the beach and marina.
Quaint Blast From The Past - Walk To Lake/8th St - Sheboygan, WI
9.9 93 reviews
Sheboygan, WI
18/09 – 25/09
NZ$312/nighttotal: NZ$2184 (7 )

Quaint Blast From The Past - Walk To Lake/8th St

1 4
apartment , Sheboygan
This renovated two-bedroom apartment is situated in Sheboygan's historic downtown district, within walking distance of Lake Michigan and its scenic trails.
The 111.5 square metre (1200 sq ft) property sleeps six, offering a spacious layout, a media centre with record player, and is pet-friendly (non-shedding dogs only, extra fee applies).
Newly Updated! Downtown & Shore - Sheboygan, WI
9.8 6 reviews
Sheboygan, WI
18/09 – 25/09
NZ$386/nighttotal: NZ$2702 (7 )

Newly Updated! Downtown & Shore

3 4
apartment , Sheboygan
This apartment is located in a quiet residential neighbourhood in Sheboygan, just 6.4km from the city centre and 8km from the Lake Michigan shoreline. It has received excellent user ratings, making it a popular choice for travellers.
The property has three bedrooms and one bathroom, comfortably accommodating up to six guests. It offers a fully equipped kitchen, a garden, free on-site laundry facilities, and pet-friendly accommodation for up to two dogs.
The Historic Downtown Suite - Sheboygan, WI
9.6 7 reviews
Sheboygan, WI
04/07 – 06/07
NZ$466/nighttotal: NZ$932 (2 )

The Historic Downtown Suite

2 2
apartment , Sheboygan Falls
This Historic Downtown Suite in Sheboygan Falls offers a convenient location close to local shops and restaurants, and is 10km from the Children's Museum.
The 74 square metre apartment features two bedrooms, one bathroom, and sleeps up to ten guests, boasting a fully equipped kitchen, private balcony, free Wi-Fi, and free private parking.

Best Sheboygan, WI holiday rentals with a pool

Among the 274 accommodations in Sheboygan, WI, here are the 2 best rentals with a pool

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
26/07 – 30/07
NZ$2010/nighttotal: NZ$8040 (4 )

Luxury Pool Retreat-2 Acres-near Whistling Straits

1 4
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

Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit - Sheboygan, WI
10 7 reviews
Sheboygan, WI
18/09 – 25/09
NZ$467/nighttotal: NZ$3269 (7 )

Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit

3 4
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.
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.
Sheboygan Riverside Condo - Sheboygan, WI
10 1 review
Sheboygan, WI
10/08 – 13/08
NZ$758/nighttotal: NZ$2274 (3 )

Sheboygan Riverside Condo

2 2
apartment , Sheboygan
This three-bedroom, two-bathroom flat in Sheboygan offers a riverfront location with a private balcony, just 1.2 kilometres from the Above & Beyond Children's Museum and 3.5 kilometres from Blackwolf Run.
This accommodation sleeps six guests and features a modern kitchen with a fridge, microwave oven, and dishwasher, air conditioning, internet, a terrace, and a two-car garage, with proximity to Blue Harbor Resort & Conference Center Water Park and Bookworm Gardens.
Sheboygan Getaway With Deck And On-site Lake Access! - Sheboygan, WI
9.0 1 review
Sheboygan, WI
18/09 – 25/09
NZ$582/nighttotal: NZ$4074 (7 )

Sheboygan Getaway With Deck And On-site Lake Access!

2 4
apartment , Sheboygan
This Sheboygan apartment offers convenient access to General King Park Beach (a 0.8km walk) and South Side Municipal Beach (1.9km away), providing easy access to Lake Michigan.
The 93 square metre, two-bedroom flat sleeps nine guests and features a fully equipped kitchen, private balcony, in-unit laundry, free Wi-Fi, and on-site parking, plus access to a lake for swimming.

Best Sheboygan, WI holiday rentals with parking

Cozy Lake Michigan Cottage Direct Lakefront Views Of Lake Michigan Premier Host! - Sheboygan, WI
9.8 258 reviews
Sheboygan, WI
26/07 – 30/07
NZ$702/nighttotal: NZ$2808 (4 )

Cozy Lake Michigan Cottage Direct Lakefront Views Of Lake Michigan Premier Host!

2 4
apartment , Sheboygan
This waterfront house is located near the St Peter Claver Parish, less than 1.6 kilometres from the Lake Michigan shoreline and within 3.2 kilometres of the Blue Harbor Resort & Conference Center Water Park.
This 88 square metre house sleeps up to six guests and boasts a terrace, garden, spa and parking, as well as a fully equipped kitchen, fireplace, and free Wi-Fi.
Newly Updated! Downtown & Shore - Sheboygan, WI
9.9 42 reviews
Sheboygan, WI
06/08 – 09/08
NZ$541/nighttotal: NZ$1623 (3 )

Newly Updated! Downtown & Shore

1 2
apartment , Sheboygan
This apartment in Sheboygan is conveniently located just 4 kilometres from the city centre and 5 kilometres from the lakeshore, offering easy access to restaurants, shops, and beaches. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is spacious and can accommodate up to 6 guests, with comfortable queen-sized beds in each bedroom. Guests can enjoy a fully equipped kitchen, free laundry facilities, and peaceful nights with blackout shades and white noise machines.
Sheboygan Sunrise Beach Stay - Sheboygan, WI
10 6 reviews
Sheboygan, WI
18/09 – 25/09
NZ$362/nighttotal: NZ$2534 (7 )

Sheboygan Sunrise Beach Stay

2 4
apartment , Sheboygan
This Sheboygan apartment, a first-floor condo in the Ellis Historical District, is situated steps from Lake Michigan and within easy walking distance of Sheboygan's restaurants, bars, and the Riverwalk, offering proximity to the John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts.
The two-bedroom, one-bathroom flat sleeps up to six guests, featuring a fully equipped kitchen, two queen bedrooms with TVs and internet access, a pull-out sofa bed, keyless entry, and free on-street parking.
Vintage Sheboygan - Sheboygan, WI
9.4 140 reviews
Sheboygan, WI
10/08 – 13/08
NZ$272/nighttotal: NZ$816 (3 )

Vintage Sheboygan

3 2
apartment , Sheboygan
This three-bedroom apartment in Sheboygan is located just 1.6 kilometres from the Lake Michigan beach and within walking distance of the 8th Street restaurants.
The apartment features a spacious living room, an eat-in kitchen with a separate butler's pantry, and a bathroom with a clawfoot tub shower enclosure, offering ample space for a comfortable stay.
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