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

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.
Updated Victorian In The Heart Of Sheboygan. Beach, Downtown, Golf, Road America - Sheboygan, WI
10 109 reviews

Updated Victorian In The Heart Of Sheboygan. Beach, Downtown, Golf, Road America

apartment, Sheboygan
This family-friendly holiday home is located just 1.6km from Lake Michigan and North Side Municipal Beach, offering a peaceful escape close to the water's edge. The property has consistently received excellent ratings for user experience, location and cleanliness.
This three-bedroom property comfortably accommodates up to nine guests. Enjoy a range of amenities including a fully equipped kitchen, a swimming pool, a spa, a terrace, a garden and free Wi-Fi.
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.
Spacious/stylish, 2br Loft - Sheboygan, WI
9.9 130 reviews

Spacious/stylish, 2br Loft

apartment, Sheboygan
This apartment is situated in a walkable neighbourhood in Sheboygan, just a short distance from shops, restaurants, museums, and the lakefront. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
This two-bedroom, one-bathroom home can comfortably accommodate up to six guests. It features a well-equipped kitchen, in-unit laundry, smart TVs, free Wi-Fi, and convenient parking.

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 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.

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

Two Bedroom Home Away From Home - Ryder Cup!!! - Sheboygan, WI
10 3 reviews

Two Bedroom Home Away From Home - Ryder Cup!!!

apartment, Sheboygan
This two-bedroom apartment is located in a central area of Sheboygan, just 1.6-3.2 kilometres from shops and restaurants, and 14.5 kilometres from Whistling Straits Golf Course. It has received excellent ratings for location, cleanliness, and user experience.
The flat can accommodate up to six guests and features a fully equipped kitchen, a farmhouse-style dining table, a 50-inch TV with entertainment options, comfortable bedrooms, laundry facilities, and an additional queen-size air mattress.
A Glorious Getaway Sheboygan - Lux Lake Condo - Sheboygan, WI
9.5 13 reviews

A Glorious Getaway Sheboygan - Lux Lake Condo

apartment, Sheboygan
This four-bedroom condo is located in Sheboygan's South Pier District, just 730 metres from Lake Michigan's sandy beach and boardwalk, and a short distance from attractions such as The American Club and Kohler Waters Spa.
This spacious 185-square-metre residence accommodates up to 12 guests with four bedrooms and three bathrooms, including a master suite with a jacuzzi, and offers a fully equipped kitchen, private balcony, and in-unit laundry facilities.
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.
Downtown 4br-game Room  5 Walk To Lake, Pets Ok! - Sheboygan, WI
9.8 59 reviews

Downtown 4br-game Room 5 Walk To Lake, Pets Ok!

apartment, Sheboygan
This apartment is situated in downtown Sheboygan, just a short walk from the beach, restaurants, and nightlife, making it an ideal base for exploring the town. The apartment consistently receives excellent ratings for location, cleanliness, and user experience.
This four-bedroom, two-bathroom dwelling can comfortably accommodate up to eleven guests. The apartment offers a range of amenities including a fully equipped kitchen, air conditioning, parking, and internet access, ensuring a comfortable and enjoyable stay.

Best pet-friendly Sheboygan, WI holiday apartments

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

Close To Downtown & Shore | Great Location - Sheboygan, WI
9.0 10 reviews

Close To Downtown & Shore | Great Location

apartment, Sheboygan
This apartment is located in a quiet residential neighbourhood in Sheboygan, just 6.4km from the city centre and 8km from the Lake Michigan shoreline. It has received excellent user ratings, making it a popular choice for travellers.
The property has three bedrooms and one bathroom, comfortably accommodating up to six guests. It offers a fully equipped kitchen, a garden, free on-site laundry facilities, and pet-friendly accommodation for up to two dogs.
Lovely Modern Home With Fire Pit - Sheboygan, WI
10 50 reviews

Lovely Modern Home With Fire Pit

apartment, Sheboygan
This Sheboygan apartment, ideally situated in a central location, offers easy access to local attractions such as Road America and the beaches, though precise distances aren't specified.
The self-contained flat comprises one bedroom, one bathroom, and accommodates two guests; features include a private backyard with a fire pit, a dedicated workspace, and convenient parking options for both compact and larger vehicles.
Spacious Getaway  Near Lake & Downtown  Garden - Sheboygan, WI
10 4 reviews

Spacious Getaway Near Lake & Downtown Garden

apartment, Sheboygan
This charming 1930s brick house is situated just a few blocks from Lake Michigan and Sheboygan's downtown area, with Whistling Straits a 16km drive away. The property consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The house has four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a fully equipped kitchen, a relaxing backyard with a patio, and the convenience of off-street parking.
Designer Victorian Near Lake Michigan & Downtown - Sheboygan, WI
9.9 144 reviews

Designer Victorian Near Lake Michigan & Downtown

apartment, Sheboygan
This charming Victorian house is located in a peaceful neighbourhood just a kilometre from Lake Michigan and a short distance from Sheboygan's city centre, golf courses, and restaurants. The property has excellent ratings for location, cleanliness, and user experience.
This five-bedroom house can comfortably accommodate eight guests, with two bathrooms and an additional sleeping area in the sunroom. The property offers a fully equipped kitchen, a private garden with a barbecue, a hammock, and a deck, plus a fitness centre, parking, and air conditioning.
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