Best apartment offers in Sheboygan, WI

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Sheboygan, WI apartments
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334 Holiday apartments 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

Coastal Comfort Near Lake Mi & Downtown - Sheboygan, WI
9.8 131 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+.
Summer Plans?  Beat The Crowds And Get The Dates You Want! - Sheboygan, WI
9.8 85 reviews

Summer Plans? Beat The Crowds And Get The Dates You Want!

apartment, Sheboygan
This spacious 10-bedroom mansion is located on a bluff overlooking Lake Michigan in Sheboygan, just a short walk from the beach, marina, and various cultural attractions. It has received excellent user ratings, making it a popular choice for travellers. This luxurious property spans 994 square metres and comfortably accommodates up to 24 guests. The mansion offers a range of amenities, including a fully equipped kitchen, a lower-level tavern, a veranda with outdoor fire tables, a gas grill, 4 kayaks, a playground, and a nearby indoor water park, making it ideal for families and groups.
Sleeps 7{spacious}pets Welcome! - Sheboygan, WI
9.4 3 reviews

Sleeps 7{spacious}pets Welcome!

apartment, Sheboygan
This three-bedroom lakeside apartment in Sheboygan is situated 1.8 km from HSHS St. Nicholas Hospital and 2.4 km from Lake Michigan, offering easy access to the Sheboygan County Historical Museum and Above & Beyond Children's Museum.
The 7-guest property features a fully equipped kitchen, in-unit laundry, free Wi-Fi, a Smart TV, and a private garden, all within a smoke-free environment; enjoy nearby lake activities and serene views.
Riverfront Condo Steps To Dining & Lake Michigan - Sheboygan, WI
10 14 reviews

Riverfront Condo Steps To Dining & Lake Michigan

apartment, Sheboygan
This riverfront flat in Sheboygan's South Pier District offers a peaceful escape, just 300 meters from downtown's shops and restaurants, and a short walk to Southside Beach and the Lake Michigan pier.
This spacious 3-bedroom, 2-bathroom condo accommodates up to six guests, featuring a fully equipped kitchen, a living room with a fireplace, air conditioning, a private balcony with water views, and allowing pets.

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

Among the 334 accommodations in Sheboygan, WI, here are the 1 best apartments with a pool

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 malted milk. The city also boasts a beautiful lakeside location on Lake Michigan, offering stunning views and recreational opportunities. Its German heritage is also strongly reflected in its architecture and cultural events.
  • 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 Marsh Wildlife Area for birdwatching and nature trails. The John Michael Kohler Arts Center, while not unknown, offers unique and often overlooked exhibits. A quieter, less-visited part of the lakefront is found north of the main downtown area. Consider a stroll along the less-trafficked sections of the Sheboygan Riverwalk.
  • What are the best apartments with a pool in Sheboygan, WI?

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

    Summer (June-August) offers warm weather perfect for enjoying the lakefront and outdoor activities. Autumn (September-October) provides beautiful fall colours and a pleasant climate. The best time depends on your preferences; if you enjoy winter activities, then visiting during the winter months (November-March) might be ideal, though it can be cold.
  • What are the best apartments with a jacuzzi in Sheboygan, WI?

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

    Sheboygan's festivals often celebrate its German heritage. While specific annual dates change, look for events celebrating local crafts and food that often feature traditional German fare and music. Check local listings closer to your travel dates for current information on festivals.
  • 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's location on Lake Michigan makes water sports popular, including boating, swimming, and fishing. The city also has excellent cycling paths and several parks suitable for walking, jogging, or picnicking. Golfing is also a popular pastime in the area.
  • What are the best pet friendly apartments in Sheboygan, WI?

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

    Visiting local businesses, such as independent shops and restaurants, is a great way to interact with residents. Attending community events or festivals offers further opportunities to chat with locals and learn about the city's heritage and traditions. Striking up conversations in local pubs or cafes can also be fruitful.
  • What are the best apartments with parking in Sheboygan, WI?

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

    Sheboygan is known for its cheese, so trying local cheese varieties is a must. Many restaurants serve traditional German dishes, including sausages and pretzels. Local breweries also offer a range of craft beers to sample.
  • What specific items should one pack for a trip to Sheboygan, Wisconsin?

    Pack comfortable walking shoes, as you'll likely be doing a fair amount of walking. Layers of clothing are advisable, as the weather can be unpredictable. Sunscreen, a hat, and sunglasses are essential during the summer months. If visiting during colder months, pack warm clothing, including a coat, hat, gloves, and scarf.
  • What are the top sights to visit in Sheboygan, Wisconsin?

    The Sheboygan Riverwalk offers scenic views and access to many attractions. The Wisconsin Maritime Museum is a popular choice, showcasing the area's maritime history. The Blue Harbor Resort and Spa is a luxurious resort with a variety of amenities. The historic downtown area, with its unique shops and architecture, is also worth exploring.

Nearby regions

Best Sheboygan, WI holiday apartments with air conditioning

Chic 1-bedroom Apartment With Wifi, Ac In Fabulous Sheboygan - Sheboygan, WI
9.6 30 reviews

Chic 1-bedroom Apartment With Wifi, Ac In Fabulous Sheboygan

apartment, Sheboygan
This Sheboygan apartment rental is situated in the Ellis Historical District, a short distance from Deland Park and an 8-minute walk (approximately 0.64 km) from Lake Michigan.
The one-bedroom, one-bathroom flat sleeps two guests and offers a fully equipped kitchen, Wi-Fi, a smart TV, and is close to attractions such as the Above & Beyond Children's Museum and the Blackwolf Run golf course.
Pelican Point - Private Retreat - Sheboygan, WI
10 8 reviews

Pelican Point - Private Retreat

apartment, Sheboygan
This lakeside Cape Cod-style house in Sheboygan overlooks Lake Michigan and the Black River, offering privacy and serenity.
Sleeping up to twelve guests, this four-bedroom, two-and-a-half-bathroom property boasts a spacious primary suite, sunroom, two-car garage, and a future direct water access, alongside a fully equipped kitchen including a dishwasher and fridge-freezer.
30 Second Walk - Lake Michigan - Sheboygan, WI
10 16 reviews

30 Second Walk - Lake Michigan

apartment, Sheboygan
This spacious four-bedroom, three-bathroom flat offers unparalleled proximity to Lake Michigan, situated just 30 metres from its shores in a peaceful Sheboygan neighbourhood, and directly across from a scenic park.
This family-friendly property boasts 344 square metres of living space, featuring a kitchen with a fridge, freezer, microwave oven, and dishwasher, air conditioning, garden, and parking, accommodating up to ten guests with excellent user, location, and cleanliness ratings.
Dog-friendly Sheboygan Home - 1 Mi To Town! - Sheboygan, WI
9.8 38 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).

Best pet-friendly Sheboygan, WI holiday apartments

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

The Suncatcher -Steps From Lake - Fenced Yard - Sheboygan, WI
10 102 reviews

The Suncatcher -Steps From Lake - Fenced Yard

apartment, Sheboygan
This Sheboygan holiday home, situated one block from Lake Michigan and a short walk from the city centre, offers easy access to the Farmers Market, Deland Park, and is within a 24km drive of Whistling Straits and Black Wolf Run.
Sleeping up to eight guests in three bedrooms and two bathrooms, the property boasts a fully equipped kitchen with staples provided, a fenced backyard with a propane grill, plus family-friendly amenities including a pack 'n play, high chair, and children's play area.
4- Bedroom Retreat With Sauna, Game Room, Patio & Walk To Bars & Restaurants - Sheboygan, WI
10 2 reviews

4- Bedroom Retreat With Sauna, Game Room, Patio & Walk To Bars & Restaurants

apartment, Sheboygan
This Sheboygan apartment, ideally located for exploring the city centre, offers easy walking access to numerous restaurants, bars, and nightlife venues.
The four-bedroom, two-bathroom dwelling sleeps thirteen guests and boasts a fully equipped games room with a pool table and air hockey, a private sauna, and a large outdoor gazebo with barbecue facilities, all within proximity of the Stefanie H. Weill Center and John Michael Kohler Arts Center.
The Suncatcher- Steps To Lake Michigan. Pet Friendly & Fully Fenced - Sheboygan, WI
10 42 reviews

The Suncatcher- Steps To Lake Michigan. Pet Friendly & Fully Fenced

apartment, Sheboygan
This Sheboygan apartment offers a superb lakeside location, moments from Lake Michigan and a short walk (less than 1 km) from Sheboygan's city centre shops and restaurants, with Whistling Straits and Black Wolf Run golf courses approximately 24 km away.
Sleeping eight guests, this three-bedroom, two-bathroom holiday let boasts a fully equipped kitchen, family-friendly amenities including a Pack & Play and high chair, a private garden with barbecue and games, plus beach essentials for Lake Michigan use.
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.
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