Best apartment offers in Sheboygan, WI

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Sheboygan, WI apartments
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334 Best apartments in Sheboygan, WI

Best family friendly Sheboygan, WI Holiday Apartments and Self Catering Accommodations

Among the 334 accommodations in Sheboygan, WI, here are the 4 best family friendly holiday apartments

Boat House | Upper Unit, Walk To Beach & Downtown - Sheboygan, WI
No reviews

Boat House | Upper Unit, Walk To Beach & Downtown

apartment, Sheboygan
This upper-floor flat in Sheboygan offers a convenient location, situated a short distance from waterfront parks, bars, eateries, and the boutique shops and restaurants of downtown Sheboygan.
This pet-friendly residence accommodates up to five guests across three bedrooms, featuring a fully stocked kitchen, air conditioning, and both on-street and off-street free parking.
The Garden | Sheboygan 2 Br/1ba, Pet Friendly - Sheboygan, WI
9.7 110 reviews

The Garden | Sheboygan 2 Br/1ba, Pet Friendly

apartment, Sheboygan
The Garden apartment is located in Sheboygan, just 0.5 kilometres from Lake Michigan and a short walk from the town centre. It has received excellent ratings for cleanliness, location, and overall user experience.
This two-bedroom flat can comfortably accommodate four guests. It comes equipped with a well-stocked kitchen, fast Wi-Fi, and a cosy living room, perfect for relaxing after a day exploring Sheboygan.
Logan's Guest Nest - Sheboygan, WI
9.9 232 reviews

Logan's Guest Nest

apartment, Sheboygan
Logan's Guest Nest is located in a quiet, small-town area of Sheboygan, just a few kilometres from Lake Michigan beaches, Road America racetrack, and various golf courses, including Whistling Straits. This property has received excellent ratings for location, cleanliness, and overall user experience.
The guest house has two bedrooms and one bathroom, accommodating up to five guests. It comes equipped with a kitchen, air conditioning, a garden, and parking, making it a comfortable and convenient base for exploring the area.
Coastal Comfort & Golfers' Paradise In Sheboygan! - Sheboygan, WI
9.4 47 reviews

Coastal Comfort & Golfers' Paradise In Sheboygan!

apartment, Sheboygan
This holiday home is located in the Ellis Historical District of Sheboygan, less than 800 metres from Lake Michigan and a short walk to Deland Park. It has received excellent reviews from previous guests, making it a popular choice for travellers visiting the area.
The property has three bedrooms and two bathrooms, spanning 93 square metres and comfortably accommodating up to six guests. The home offers a range of amenities including a fully equipped kitchen, a spa, air conditioning, free Wi-Fi, and parking, making it a perfect base for exploring the local area.

Best Holiday Apartments and Self Catering Accommodations in Sheboygan, WI with a pool

Among the 334 accommodations in Sheboygan, WI, here are the 2 best apartments with a pool

Your Own Private Resort For The Ryder Cup! - Sheboygan, WI
10 1 review

Your Own Private Resort For The Ryder Cup!

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.
Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
10 10 reviews

Luxury Pool Retreat-2 Acres-near Whistling Straits

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 apartment rentals in Sheboygan, WI

  • What is Sheboygan, Wisconsin, famous for?

    Sheboygan is known for its rich history in manufacturing, particularly its legacy in the production of cheese and plastics. The city also boasts a beautiful lakeside setting on the shores of Lake Michigan, offering stunning views and recreational opportunities. It's also recognised for its vibrant arts scene and its charming downtown area.
  • What are the best apartments in Sheboygan, WI?

  • What are some off-the-beaten-path spots to check out in Sheboygan, Wisconsin?

    For something different, explore the Sheboygan Riverwalk, a scenic path perfect for a stroll or cycle. The Vollrath Company Museum offers a fascinating glimpse into the history of the city's manufacturing heritage. For a quieter experience, consider visiting the Wetlands Preserve, a haven for birdwatching and nature walks.
  • What are the best apartments with a pool in Sheboygan, WI?

  • When should one visit Sheboygan, Wisconsin, for the best experience?

    The best time to visit Sheboygan is during the summer months (June-August) for warm weather ideal for enjoying the lakefront and outdoor activities. Autumn (September-October) offers beautiful foliage and a pleasant climate. Spring and winter each have their own unique charm, but might be less ideal for certain activities.
  • What are the best apartments with a jacuzzi in Sheboygan, WI?

  • Are there any cultural festivals unique to Sheboygan, Wisconsin?

    Sheboygan has several festivals throughout the year. The Bratwurst Festival is a major event, celebrating the city's famous bratwurst. Other events often include art fairs and music festivals which change annually, so checking local listings closer to your travel dates is recommended.
  • What are the best apartments for families and kids in Sheboygan, WI?

  • What sports or recreational activities are a big draw in Sheboygan, Wisconsin?

    Sheboygan offers many recreational opportunities. The city's location on Lake Michigan makes it a popular spot for boating, swimming, and fishing. The Sheboygan County Fairgrounds hosts various events, and there are numerous parks and trails for cycling, hiking and walking. The city also has a number of golf courses.
  • What are the best pet friendly apartments in Sheboygan, WI?

  • How can one best interact with locals to learn about Sheboygan, Wisconsin's traditions?

    The best way to learn about local traditions is to strike up conversations with people in local businesses, such as cafes and shops in the downtown area. Visiting local pubs or attending community events can also offer opportunities to interact with residents and learn more about the city's culture.
  • What are the best apartments with parking in Sheboygan, WI?

  • What are the best local dishes to try in Sheboygan, Wisconsin?

    Sheboygan is renowned for its bratwurst, a local specialty. Many restaurants and establishments serve variations of this sausage. Local seafood is also worth trying, given the city's lakeside location. Look for fresh fish dishes at restaurants along the waterfront.
  • What specific items should one pack for a trip to Sheboygan, Wisconsin?

    Pack comfortable walking shoes as you'll likely be doing a fair bit of exploring on foot. Layers of clothing are recommended, as the weather can be unpredictable. Don't forget swimwear if you plan on enjoying the lake, and sunscreen and a hat are essential during the summer months.

Nearby regions

Best Sheboygan, WI holiday apartments with air conditioning

Janelle's Dockside Condo - Sheboygan, WI
9.9 123 reviews

Janelle's Dockside Condo

apartment, Sheboygan
This two-bedroom apartment is located in Sheboygan's South Pier District, just a short walk from the boardwalk and its attractions, offering easy access to the area's charm and attractions. It has received excellent ratings for location, cleanliness, and overall guest experience.
The property has two bathrooms and can accommodate up to four guests. The apartment comes equipped with modern amenities, including a fully equipped kitchen, air conditioning, and a private deck overlooking Lake Michigan. Guests can enjoy the nautical theme, explore the nearby golf courses, or simply relax and take in the scenic views.
Lake Michigan View Steps Beach - Sheboygan, WI
No reviews

Lake Michigan View Steps Beach

apartment, Sheboygan
This two-bedroom, two-bathroom apartment in Sheboygan offers exceptional Lake Michigan views and is within walking distance of the Sheboygan Arts Center and Stefanie Weil Theatre.
The self-catering flat sleeps four guests and includes amenities such as air conditioning, parking, and internet access; its prime location allows easy exploration of Sheboygan's attractions and dining options.
Lg Executive Home, Kohler Golf, Eaa, Road America - Sheboygan, WI
No reviews

Lg Executive Home, Kohler Golf, Eaa, Road America

apartment, Sheboygan
This six-bedroom home is located just 6.4 kilometres from Kohler Golf and the American Club, in a peaceful wooded area. The property is ideal for large groups or families, with space for up to 14 guests.
The home features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as a garden, a fitness centre, and parking. Enjoy the outdoors on the brick patio with a gas grill, or relax by the fire pit or wood-burning campfire.
Luxury Lakeside Home-new Renovation-walk To Beach, Dining, & More. - Sheboygan, WI
10 15 reviews

Luxury Lakeside Home-new Renovation-walk To Beach, Dining, & More.

apartment, Sheboygan
This modern farmhouse sits just 0.8 kilometres from Lake Michigan's shores on Sheboygan's Northside, offering easy access to the city's beaches, parks, and walking paths. The property has earned an excellent user rating, so you can be sure of a comfortable and enjoyable stay.
The house has four bedrooms and two bathrooms, providing space for up to eight guests, and covers 150 square metres. You'll find a fully-equipped kitchen with a dishwasher, a garden, a spa, and parking, along with central air conditioning and luxury linens.

Best pet-friendly Sheboygan, WI holiday apartments

Among the 334 accommodations in Sheboygan, WI, here are the 4 best pet friendly holiday apartments

Dog-friendly Sheboygan Home - 1 Mi To Town! - Sheboygan, WI
9.8 37 reviews

Dog-friendly Sheboygan Home - 1 Mi To Town!

apartment, Sheboygan
This Sheboygan holiday home, near Kiwanis Park, Bookworm Gardens, and South Shore Beach, offers easy access to Sheboygan's attractions.
The single-storey property sleeps two in one bedroom and one bathroom, boasting a fully equipped kitchen with modern appliances, a patio with gas grill, two Smart TVs, and pet-friendly facilities (dogs only, maximum two, fee applies).
Beautiful 1920s Georgian Revival Manor Home - Sheboygan, WI
10 3 reviews

Beautiful 1920s Georgian Revival Manor Home

apartment, Sheboygan
This charming apartment is located in the historic North Point neighbourhood of Sheboygan, just across the street from a long flight of stairs leading to the mile-long Lake Michigan beachfront at Deland Park. It has received excellent ratings for its location, cleanliness and overall experience.
The property offers three bedrooms and one bathroom, accommodating up to seven guests. Amenities include a fully equipped kitchen, a sunroom with a twin bed, a gas fireplace, a garden, a bar, parking, and air conditioning.
The Links! - Luxury Golf Retreat - Sheboygan, WI
10 30 reviews

The Links! - Luxury Golf Retreat

apartment, Sheboygan
This luxurious four-bedroom house near Whistling Straits and Blackwolf Run in Sheboygan, Wisconsin, offers easy access to these world-renowned golf courses.
Sleeping eight guests, this self-catering property boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), an OptiShot Nova golf simulator, GoldenTee arcade game, and foosball table, alongside three bathrooms and ample living space.
Black River Retreat - Sheboygan, WI
9.7 45 reviews

Black River Retreat

apartment, Sheboygan
This four-bedroom Cape Cod-style house is located in Sheboygan's Black River neighbourhood, a short distance from Sheboygan's city centre, Kohler-Andrae State Park, and Lakeview Park.
The spacious property, sleeping up to six guests, boasts a large upstairs suite with private bathrooms, a kids' zone, an eclectic study with vintage features, a garden exceeding 0.4 hectares, and is close to Road America and local golf courses.
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