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

Serene Home One Block From Lake Michigan - Sheboygan, WI
9.7 244 reviews
Sheboygan, WI
06/08 – 09/08
$833/nighttotal: $2499 (3 )

Serene Home One Block From Lake Michigan

3 2
apartment , Sheboygan
This apartment is located just a block from Lake Michigan and Deland Park in Sheboygan, within walking distance of North Beach and the YMCA, and minutes from the town centre. The property has excellent user, location, and cleanliness ratings, making it a great choice for travellers looking for a comfortable and convenient stay.
The apartment is a two-storey property with three bedrooms, two bathrooms and can accommodate up to six guests. It has a fully equipped kitchen with a fridge, microwave and dishwasher, as well as air conditioning and parking. Guests can enjoy relaxing by the lake or exploring the nearby golf courses, shops, and restaurants.
Remodeled Home On Lake Michigan - Sheboygan, WI
10 327 reviews
Sheboygan, WI
24/07 – 26/07
$815/nighttotal: $1630 (2 )

Remodeled Home On Lake Michigan

3 2
apartment , Sheboygan
This three-bedroom apartment is situated just south of Sheboygan's city centre, a short walk from restaurants, shops, and entertainment, and less than 1km from two public parks with beaches. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 135 square metres of space, comfortably accommodating up to seven guests. It features a fully equipped kitchen, a spacious living area, a private terrace, and a garden, providing a comfortable and relaxing stay.
Breezy Condo W/ Fireplace & Balconies - Sheboygan, WI
9.9 148 reviews
Sheboygan, WI
10/08 – 13/08
$559/nighttotal: $1677 (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.
Sheboygan Falls: Rochester Ranch 3bed/1bath - Sheboygan, WI
10 2 reviews
Sheboygan, WI
10/08 – 13/08
$319/nighttotal: $957 (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.

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

Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit - Sheboygan, WI
10 7 reviews
Sheboygan, WI
06/08 – 09/08
$765/nighttotal: $2295 (3 )

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

3 2
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.
At River's Edge - Charming 2br River Retreat With Garage - Sheboygan, WI
Sheboygan, WI
06/08 – 09/08
$727/nighttotal: $2181 (3 )

At River's Edge - Charming 2br River Retreat With Garage

2 2
apartment , Sheboygan
This waterfront flat in Sheboygan, located on the Sheboygan River, offers serene views and is within minutes of Lake Michigan, downtown dining, and local attractions such as Deland Park.
This two-bedroom flat accommodates up to six guests and features a king suite with a private balcony, a second bedroom with two queen beds, in-unit laundry, and an attached two-car garage, with the Sheboygan Riverwalk just a short walk away.
Pet-friendly Sheboygan Home, 1 Mi To Lake Michigan - Sheboygan, WI
9.8 59 reviews
Sheboygan, WI
10/08 – 13/08
$900/nighttotal: $2700 (3 )

Pet-friendly Sheboygan Home, 1 Mi To Lake Michigan

4 2
house , Sheboygan
This pet-friendly house is located just 1.6km from the beautiful Lake Michigan shoreline, within walking distance of the Children's Museum and a short drive from both North Side and South Side Municipal Beaches. The property has received excellent ratings for location, cleanliness, and user satisfaction.
The house provides spacious accommodation for up to 10 guests with 4 bedrooms and 1 bathroom spread across 279 square metres. Guests can enjoy a fully equipped kitchen, a terrace, a garden, a spa, air conditioning, parking, and free Wi-Fi.
Spacious Home Near Lake Mi W Fire Pit - Sheboygan, WI
9.4 13 reviews
Sheboygan, WI
25/07 – 26/07
$793/nightfor 1 night

Spacious Home Near Lake Mi W Fire Pit

3 6
house , Sheboygan
This spacious Sheboygan house, a short 0.8 km stroll from General King Park Beach and a few kilometres from the Children's Museum, offers convenient access to Sheboygan's attractions and Milwaukee.
The 158 square metre property sleeps up to 11 guests in three bedrooms, boasting a fully equipped kitchen, air conditioning, a garden, parking, and an indoor play area, ideal for families.

Best Sheboygan, WI vacation rentals with parking

Lux Uptown Escape - The Trester\n - Sheboygan, WI
9.6 11 reviews
Sheboygan, WI
20/09 – 25/09
$307/nighttotal: $1535 (5 )

Lux Uptown Escape - The Trester\n

2 4
apartment , Sheboygan
This two-bedroom, two-bathroom apartment in Sheboygan's Uptown district offers easy walking access to Sheboygan's theatre and restaurants, and is a short drive from Lake Michigan and Kohler-Andrae State Park.
The 1885 property features a fully equipped kitchen, private garden with a barbecue and outdoor cinema screen, sleeping up to four guests, and includes parking and Wi-Fi.
New Riverfront Loft - Fantastic Location W/stunning Views - On The Boardwalk! - Sheboygan, WI
10 9 reviews
Sheboygan, WI
18/09 – 25/09
$393/nighttotal: $2751 (7 )

New Riverfront Loft - Fantastic Location W/stunning Views - On The Boardwalk!

1 4
apartment , Sheboygan
This Sheboygan flat offers a prime downtown and waterfront position on the boardwalk, boasting riverfront views and immediate access to the John Michael Kohler Arts Centre (200 metres) and Kohler-Andrae State Park (3 kilometres).
This family-friendly accommodation includes air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher and microwave, and a unique lobster pot for cooking, with laundry services available and proximity to Blue Harbor Resort Waterpark and Above & Beyond Children's Museum.
The Beach Town Bungalow - Sheboygan, WI
Sheboygan, WI
24/07 – 26/07
$627/nighttotal: $1254 (2 )

The Beach Town Bungalow

2 3
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.
Fresh Coast Craftsman - Pet Friendly | Near Lake - Sheboygan, WI
10 1 review
Sheboygan, WI
26/07 – 30/07
$339/nighttotal: $1356 (4 )

Fresh Coast Craftsman - Pet Friendly | Near Lake

1 4
apartment , Sheboygan
This two-bedroom flat is located in a residential district of Sheboygan, offering convenient access to city amenities and the Great Lakes, approximately 5 kilometres away.
This pet-friendly residence accommodates up to four guests and includes a secure two-car garage, on-site laundry facilities, a smart TV, and a fully fenced garden, making it ideal for families or groups seeking a comfortable stay with all necessary conveniences.
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