Best apartment offers in Sheboygan, WI

334 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Sheboygan, WI apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Beachfront Holiday House On The Lake - Sheboygan, WI
10 5 reviews

Beachfront Holiday House On The Lake

apartment, Sheboygan
This five-bedroom house, ideal for large groups, enjoys a superb location in Sheboygan, directly opposite North Beach and Peace Park, and within a short distance (less than 0.5 km) of the town centre and marina.
Sleeping up to twelve guests, the property boasts three bathrooms, a fully equipped kitchen, two washing machines and dryers, plus extensive outdoor space including a rooftop deck, screened patio, and sunroom overlooking Lake Michigan, alongside ample indoor living space spread across three floors, offering board games and access to streaming services.
Waterfront Sheboygan Condo - Sheboygan, WI
9.4 7 reviews

Waterfront Sheboygan Condo

apartment, Sheboygan
This riverfront condominium is situated on Sheboygan's boardwalk, offering direct views and a 5-minute walk to South Shore Beach, local eateries, and shops.
This spacious, two-storey dwelling accommodates up to 12 guests across 3 bedrooms and a loft, featuring a fully equipped kitchen, in-unit laundry, elevator access, and provided beach essentials for exploring nearby attractions such as Deland Park and Kohler Andrae State Park.
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.
Beachy 3-bedroom Upper With Wifi And Ac Minutes From Lake Michigan - Sheboygan, WI
9.8 9 reviews

Beachy 3-bedroom Upper With Wifi And Ac Minutes From Lake Michigan

apartment, Sheboygan
This three-bedroom Sheboygan apartment offers self-check-in via keyless touchpad and is conveniently located near Lake Michigan, providing easy access to attractions such as Whistling Straits and Kohler-Andrae State Park.
The spacious property sleeps five guests comfortably, boasting a fully equipped kitchen, a backyard with a fire pit, a smart TV with streaming services, and a bathroom stocked with essentials; nearby street parking is readily available.

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

Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
10 16 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.
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.

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

At River's Edge | 2br River Retreat With Garage - Sheboygan, WI
10 7 reviews

At River's Edge | 2br River Retreat With Garage

apartment, Sheboygan
This spacious 2-bedroom apartment is situated on the Sheboygan River, offering direct access to the Sheboygan Riverwalk and within 1 kilometre of Lake Michigan beaches, the Sheboygan Lighthouse, Deland Park, and the dining and shopping of downtown Sheboygan.
This apartment accommodates up to 6 guests across two bedrooms, one a king suite with a private balcony, fireplace and river views, and the other with two queen beds, featuring an open-plan living area, a fully equipped kitchen with a dishwasher, air conditioning, and in-unit laundry, complemented by a 2-car garage and additional parking.
Knot A Care By The Lake - Sheboygan, WI
10 11 reviews

Knot A Care By The Lake

apartment, Sheboygan
This Sheboygan apartment is situated in a historic neighbourhood, a short walk from Lake Michigan and Sheboygan's riverfront and downtown area.
The one-bedroom, one-bathroom flat offers self-catering facilities including a fridge and microwave, air conditioning, and parking; it sleeps two guests and features nautical décor in a 125+-year-old house.
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+.
The Brightside Parisian Retreat! - Near The Lake - Sheboygan, WI
10 7 reviews

The Brightside Parisian Retreat! - Near The Lake

apartment, Sheboygan
This duplex, "The Brightside & The Parisian," is located in Sheboygan, 200 meters from Lake Michigan and within easy reach of the central downtown district.
This four-bedroom, two-bathroom property accommodates up to 12 guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning and parking, making it ideal for exploring Sheboygan's amenities and waterfront.

Best pet-friendly Sheboygan, WI holiday apartments

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

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.
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.
Sheboygan Surf House -  Jetties - Sheboygan, WI
9.7 257 reviews

Sheboygan Surf House - Jetties

apartment, Sheboygan
This Sheboygan studio apartment is situated directly above EOS Surf Shop in the downtown area, a short walk from Lake Michigan's South Pier and Blue Harbor resort.
The pet-friendly self-catering apartment, sleeping up to two guests, boasts a fully equipped kitchen with an island, a queen-size bed, and a fully remodelled bathroom with a tub/shower; off-street parking is also available.
Executive 5bdrm With Fenced-in Backyard For Pets - Sheboygan, WI
No reviews

Executive 5bdrm With Fenced-in Backyard For Pets

apartment, Sheboygan
This updated five-bedroom house in Sheboygan provides a convenient base for exploring local attractions, situated within easy reach of amenities.
This spacious residence offers ample room for up to 14 guests across four floors, featuring two kitchens, two bathrooms, a game room with various activities, and a fenced-in garden with a patio and fire pit, all complemented by a dedicated "pet lounge" living area.
©2026 cozycozy.com