Compare Vacation Rentals & Airbnb in Sheboygan, WI

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Sheboygan, WI vacation rentals
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274 Rentals and Airbnb in Sheboygan, WI

Best family friendly Sheboygan, WI vacation 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
$1030/nighttotal: $3090 (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.
Spacious Home Near Lake Mi W/ Fire Pit - Sheboygan, WI
9.8 170 reviews
Sheboygan, WI
20/09 – 25/09
$262/nighttotal: $1310 (5 )

Spacious Home Near Lake Mi W/ Fire Pit

1 4
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.
Breezy Condo W/ Fireplace & Balconies - Sheboygan, WI
9.9 148 reviews
Sheboygan, WI
06/08 – 09/08
$762/nighttotal: $2286 (3 )

Breezy Condo W/ Fireplace & Balconies

2 2
apartment , Sheboygan
This second-floor apartment is located in a peaceful neighbourhood, just a short walk from the beach and the River Boardwalk, with the centre of Sheboygan and its shops, restaurants and attractions within easy reach. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment can comfortably accommodate up to five guests and features two bedrooms, a fully-equipped kitchen and two decks with stunning lake views. Guests can enjoy a range of amenities including a washer/dryer, toiletries, linens, a drip coffee pot, children's toys/games, life jackets and beach toys, high-speed Wi-Fi, a Roku TV, a desk for remote working and an electric fireplace.
Classic 5 Bedroom – Close To Beach And Downtown - Sheboygan, WI
9.9 57 reviews
Sheboygan, WI
26/07 – 30/07
$578/nighttotal: $2312 (4 )

Classic 5 Bedroom – Close To Beach And Downtown

1 4
apartment , Sheboygan
This spacious home is situated in Sheboygan, just a short walk from the beach, downtown shopping, restaurants, bars, and entertainment. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
This 5-bedroom, 2-bathroom property comfortably accommodates up to 8 guests and features a large kitchen and living area. Enjoy the convenience of a private garden, parking, and amenities like a fridge, freezer, microwave, dishwasher, and air conditioning.

Best Sheboygan, WI vacation rentals with a pool

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

Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
Sheboygan, WI
10/08 – 13/08
$1418/nighttotal: $4254 (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.
Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
10 8 reviews
Sheboygan, WI
10/08 – 13/08
$3794/nighttotal: $11382 (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.

Frequently Asked Questions about vacation rentals in Sheboygan, WI

  • What are the must-see sights in Sheboygan, Wisconsin?

    Sheboygan has a lot to offer! The Sheboygan Maritime Museum is a great place to learn about the city's rich history as a shipbuilding center. You should also check out the John Michael Kohler Arts Center, known for its unique art installations and exhibits. For a taste of local history and architecture, a stroll through the historic downtown area is a must.
  • What are the best Airbnb and vacation rentals in Sheboygan, WI?

  • Are there unique natural phenomena in Sheboygan, Wisconsin?

    While Sheboygan doesn't have dramatic, large-scale natural phenomena, its location on Lake Michigan provides beautiful lakefront views and access to beaches. The shoreline itself, with its changing dunes and the lake's impact on the landscape, is a unique feature. The wetlands and nature preserves around the city offer opportunities for birdwatching and exploring diverse ecosystems.
  • 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 Downtown Walk-up are the most popular ones.

  • What essentials should you bring along for a trip to Sheboygan, Wisconsin?

    Pack comfortable walking shoes, as you'll likely be doing a fair bit of exploring on foot. Layers are key, as the weather in Sheboygan can be unpredictable. Don't forget sunscreen, a hat, and sunglasses, especially during the summer months. And of course, a camera to capture the beautiful scenery and cityscapes.
  • What are the best vacation rentals with a pool in Sheboygan, WI?

  • What famous events or festivals are happening in Sheboygan, Wisconsin?

    Sheboygan's calendar is packed with events. The Sheboygan County Fair is a popular annual event, usually in August. The city also hosts various smaller festivals and events throughout the year, often centered around arts, culture, and the lakefront. Check local event listings closer to your travel dates for the most up-to-date information.
  • What are the best rentals for families and kids in Sheboygan, WI?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Sheboygan, Wisconsin?

    A daily budget of around $150 to $300 USD per person should be sufficient, depending on your choices. Accommodation can range from budget-friendly motels to more upscale hotels. Food costs vary, with many affordable dining options available. Transportation within the city is relatively easy and inexpensive, either by car or walking. Activity costs depend on your preferences, from free walks along the lakefront to paid entry fees for museums.
  • What are the best rentals or Airbnbs with a jacuzzi in Sheboygan, WI?

  • Where can you find the best restaurants serving local dishes in Sheboygan, Wisconsin, and what are the must-try specialties?

    Sheboygan boasts a great culinary scene. For fresh seafood, try restaurants along the lakefront. Many restaurants feature Wisconsin cheese curds as an appetizer, a must-try! Local breweries offer a chance to sample craft beers. Specific restaurant names change, so it's best to check current reviews and local guides for the most up-to-date recommendations.
  • What are some less-famous attractions in Sheboygan, Wisconsin that are worth the visit?

    The Sheboygan Riverwalk offers a pleasant stroll with views of the river and the city. Exploring the residential neighborhoods reveals charming architecture and a glimpse into daily life. The local farmers' markets, when in season, are a great way to experience local produce and interact with the community.
  • What are the best activities for engaging with locals and understanding their culture in Sheboygan, Wisconsin?

    Attending local events and festivals is a great way to meet people. Visiting the local farmers' markets allows you to interact with vendors and learn about the region's agricultural heritage. Simply striking up conversations with people you encounter while exploring the city can offer insights into local life and culture.
  • What unique natural landscapes and terrain features can travelers explore in Sheboygan, Wisconsin?

    Sheboygan's most prominent natural feature is its location on Lake Michigan. The lakefront offers sandy beaches, and the shoreline itself is a dynamic landscape shaped by the lake. The surrounding areas also include wetlands and other natural areas providing opportunities for hiking and nature walks.
  • How many days are ideal for visiting Sheboygan, Wisconsin, 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 a day exploring the downtown area and museums, a day enjoying the lakefront and beaches, and perhaps a day dedicated to exploring the surrounding natural areas or visiting nearby towns.

Nearby regions

Best Sheboygan, WI vacation rentals with a balcony

The Links! - Luxury Golf Retreat With Golf Simulator - Sheboygan, WI
10 8 reviews
Sheboygan, WI
06/08 – 09/08
$1418/nighttotal: $4254 (3 )

The Links! - Luxury Golf Retreat With Golf Simulator

4 2
apartment , Sheboygan
This four-bedroom Sheboygan dwelling is conveniently located near Blackwolf Run golf course and the Above & Beyond Children's Museum, with Deer Trace Mall and the Farmers Market also within easy reach.
The self-catering property sleeps eight guests comfortably in two king and two queen beds across four bedrooms, three bathrooms, and boasts a terrace, parking, internet access, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
Coastal 3-br Lower Near Lake Mi And Downtown Sheboygan - Sheboygan, WI
9.4 11 reviews
Sheboygan, WI
20/09 – 25/09
$271/nighttotal: $1355 (5 )

Coastal 3-br Lower Near Lake Mi And Downtown Sheboygan

3 4
apartment , Sheboygan
This three-bedroom apartment is conveniently located near Sheboygan's city centre, offering easy access to Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park.
The self-catering property sleeps five guests and includes a fully equipped kitchen, family-friendly amenities such as a travel cot and highchair, a smart TV with streaming services, and an enclosed porch; board games and puzzles are also provided.
Beachside Condo W/ Stunning Lake Views - Sheboygan, WI
10 32 reviews
Sheboygan, WI
20/09 – 25/09
$484/nighttotal: $2420 (5 )

Beachside Condo W/ Stunning Lake Views

2 4
apartment , Sheboygan
This Sheboygan beachfront apartment, less than 1.6km from St Peter Claver Parish, Blue Harbor Resort & Conference Centre, and the John Michael Kohler Arts Centre, offers direct Lake Michigan access.
The 74 square metre self-catering property features two bedrooms, one bathroom, sleeps five, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and on-site garden and barbeque facilities.
Family Home, 1 Block To Lake Michigan Beach! - Sheboygan, WI
9.9 64 reviews
Sheboygan, WI
20/09 – 25/09
$584/nighttotal: $2920 (5 )

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 vacation rentals with parking

\N\nluxury Home Historic Location 4br-3 Fullbath- Walk 3 Min Beach, 10 To Downtown - Sheboygan, WI
9.8 37 reviews
Sheboygan, WI
06/08 – 09/08
$3263/nighttotal: $9789 (3 )

\N\nluxury Home Historic Location 4br-3 Fullbath- Walk 3 Min Beach, 10 To Downtown

4 2
apartment , Sheboygan
This Sheboygan beachfront property is a five-minute walk from North Side Municipal Beach and Lake Michigan, and within a 2.4km radius of the Above & Beyond Children's Museum and the John Michael Kohler Arts Center.
This four-bedroom, three-bathroom holiday home sleeps nine guests and boasts a fully equipped kitchen, private patio, swimming pool, jacuzzi, and free Wi-Fi; enjoy easy access to Lake Michigan and local attractions.
Beachside Getaway In Sheboygan - Sheboygan, WI
10 29 reviews
Sheboygan, WI
18/09 – 25/09
$381/nighttotal: $2667 (7 )

Beachside Getaway In Sheboygan

2 4
apartment , Sheboygan
This waterfront flat is located just 1.6 kilometres from St. Peter Claver Parish and Lake Michigan, offering stunning views and easy access to local attractions. It has consistently received excellent reviews from previous guests.
The property has two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment features a fully equipped kitchen, a private patio, free Wi-Fi, and parking, making it an ideal choice for families or groups of friends.
Central Located. Seconds From The Highway To Get To Kohler, And Elkhart Lake - Sheboygan, WI
10 3 reviews
Sheboygan, WI
26/07 – 30/07
$1359/nighttotal: $5436 (4 )

Central Located. Seconds From The Highway To Get To Kohler, And Elkhart Lake

4 4
apartment , Sheboygan
This four-bedroom house is located in Sheboygan, less than 2km from Lake Michigan and just under 1.5km from HSHS St. Nicholas Hospital. It has received excellent user ratings and is perfect for families or groups of up to 14 people.
The property features a fully equipped kitchen with a fridge, microwave, dishwasher, and coffee maker, as well as a terrace, garden, and parking. Guests can enjoy amenities such as air conditioning, internet access, a washing machine, and a Smart TV.
Serene Home One Block From Lake Michigan - Sheboygan, WI
10 2 reviews
Sheboygan, WI
10/08 – 13/08
$821/nighttotal: $2463 (3 )

Serene Home One Block From Lake Michigan

3 2
house , Sheboygan
This Sheboygan holiday home is located just a few hundred metres from Lake Michigan, offering easy access to North Side Municipal Beach and the Children's Museum.
The 144 square metre property boasts three bedrooms, two bathrooms, sleeping up to eleven guests, and includes a fully equipped kitchen, free Wi-Fi, and private parking.
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