Compare Vacation Rentals & Airbnb in Sheboygan, WI

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

Best family friendly Sheboygan, WI vacation rentals

Among the 387 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals

Serene Home One Block From Lake Michigan - Sheboygan, WI
9.7 246 reviews

Serene Home One Block From Lake Michigan

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.
Coastal Comfort Near Lake Mi & Downtown - Sheboygan, WI
9.8 126 reviews

Coastal Comfort Near Lake Mi & Downtown

apartment, Sheboygan
This three-bedroom Sheboygan holiday home offers self-check-in via keyless touchpad and is conveniently located near Sheboygan's city centre, Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park (distances unspecified).
Sleeping six guests, the property features a fully equipped kitchen with complimentary staples, an enclosed porch, family-friendly amenities including a pack 'n' play and highchair, plus access to streaming services such as Netflix, Hulu, Amazon Prime, and Disney+.
Serene Home One Block From Lake Michigan - Sheboygan, WI
10 2 reviews

Serene Home One Block From Lake Michigan

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.
Cozy Corner Cottage - Dutch Colonial Step From Beach - Sheboygan, WI
10 11 reviews

Cozy Corner Cottage - Dutch Colonial Step From Beach

apartment, Sheboygan
Cozy Corner Cottage is located in Sheboygan's historic Ellis District, a short walk from Deland Park beach and within 1.6km of attractions such as the John Michael Kohler Arts Centre and the Above & Beyond Children's Museum.
This three-bedroom, two-bathroom holiday home sleeps seven guests and features a fully equipped kitchen, a smart TV, complimentary high-speed Wi-Fi, and direct beach access with provided supplies.

Best Sheboygan, WI vacation rentals with a pool

Among the 387 accommodations in Sheboygan, WI, here are the 2 best rentals with a pool

Blue Harbor Resort And Conference Center - Sheboygan, WI
8.4 523 reviews

Blue Harbor Resort And Conference Center

resort, Sheboygan
Blue Harbor Resort and Conference Center is located on the beach in Sheboygan, within 1.6 kilometres of the John Michael Kohler Arts Center, Stefanie H. Weill Center for the Performing Arts, and Above & Beyond Children's Museum. This resort has received very good user ratings.
The hotel has a range of facilities for guests, including a spa, water park, and fitness centre. It also offers a variety of amenities for families, such as a kids' club and a game room.
Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
10 9 reviews

Baronwood Oasis | Pool + Arcade Mega Estate

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

3 Blocks From Beach House 1 Bdrm Full Bath 4 Min To Downtown,sleeps 4 - Sheboygan, WI
9.8 18 reviews

3 Blocks From Beach House 1 Bdrm Full Bath 4 Min To Downtown,sleeps 4

apartment, Sheboygan
This one-bedroom flat is situated in downtown Sheboygan, a short 100-metre walk from St. Peter Claver Parish and approximately 1.3 kilometres from Lake Michigan, placing it near attractions such as the Above & Beyond Children's Museum and Blue Harbor Resort & Conference Centre Water Park.
Guests can enjoy a private terrace with outdoor furniture and a fire pit, alongside a fully equipped kitchen, in-unit laundry facilities, air conditioning, and on-site parking, with opportunities for jet skiing, kayaking, hiking, and biking nearby.
New King Park Beach Lookout Deluxe! 3br Right At Lake! - Sheboygan, WI
10 24 reviews

New King Park Beach Lookout Deluxe! 3br Right At Lake!

apartment, Sheboygan
This Sheboygan holiday home is situated less than 1.6km from Lake Michigan, St Peter Claver Parish, the Blue Harbor Resort & Conference Centre Water Park, and Aurora Clinic.
This three-bedroom, two-bathroom property sleeps ten guests and boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, a smart TV, and parking; enjoy a smoke-free environment and proximity to family-friendly attractions.
Coastal 3-br Lower Near Lake Mi And Downtown Sheboygan - Sheboygan, WI
9.4 12 reviews

Coastal 3-br Lower Near Lake Mi And Downtown Sheboygan

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.
Pet-friendly Sheboygan Home, 1 Mi To Lake Michigan - Sheboygan, WI
9.8 62 reviews

Pet-friendly Sheboygan Home, 1 Mi To Lake Michigan

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.

Best Sheboygan, WI vacation rentals with parking

Cactus Corner King Apartment - Sheboygan, WI
9.8 31 reviews

Cactus Corner King Apartment

apartment, Sheboygan
This Sheboygan apartment, ideal for up to three guests, is situated in a quiet residential area; the precise location within the city and distances to specific landmarks are not provided.
The newly remodelled, one-bedroom flat features a fully equipped kitchen, private balcony overlooking a garden, dedicated workspace with fast internet, shared laundry facilities, and ample off-street parking.
Clean, Comfy Stay Near Parks, Downtown & Lake! - Sheboygan, WI
10 56 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

apartment, Sheboygan
This two-bedroom, one-bathroom apartment in Sheboygan offers convenient access to Interstate 43, situated directly opposite Shaw Family Park and within walking distance of a Starbucks.
The 4-guest dwelling includes a kitchen, air conditioning, parking, internet access, and is close to Sheboygan's beachfront, Fireman's Park, and renowned golf courses such as Whistling Straits and Black Wolf Run (distances vary).
Sheboygan Riverside Condo - Sheboygan, WI
9.8 74 reviews

Sheboygan Riverside Condo

apartment, Sheboygan
This Sheboygan apartment, ideally located near the Sheboygan River, offers easy access to the city's attractions; precise distances to specific landmarks are not provided.
The two-bedroom, one-bathroom flat sleeps six guests and features a king suite with a private balcony and fireplace, a second bedroom with two queen beds, a modern kitchen with fridge, microwave, and dishwasher, air conditioning, a garden, parking, and a two-car garage.
Blue Horizons Hideaway Close To Downtown & Marina - Sheboygan, WI
10 6 reviews

Blue Horizons Hideaway Close To Downtown & Marina

apartment, Sheboygan
This spacious 3-bedroom, 3-bathroom flat offers a convenient location in Sheboygan, just minutes from the downtown area, the marina, and local hospitals, with the Kohler Arts Centre only 1.3 kilometres away and Kohler-Andre State Park and Whistling Straits within 6.2 to 6.3 kilometres.
This property accommodates up to six guests and features a dedicated games room, a downstairs living area with a wet bar, an outdoor fire pit, and ample parking for three trucks and boats, making it suitable for mid-term rentals.
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