Best apartment offers in Sheboygan, WI

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Sheboygan, WI apartments
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223 Holiday apartments Sheboygan, WI

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

Among the 223 accommodations in Sheboygan, WI, here are the 4 best family friendly holiday apartments

Boutique Wellness Retreat - Hot Tub And Fireplace - Sheboygan, WI
10 266 reviews
Sheboygan, WI
06/08 – 09/08
506 €/nighttotal: 1518 € (3 )

Boutique Wellness Retreat - Hot Tub And Fireplace

1 2
apartment , Sheboygan
This charming house is situated in a peaceful neighbourhood just 3 kilometres from Lake Michigan and a short distance from hiking trails, fishing spots, and restaurants, making it ideal for exploring Sheboygan. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The house comfortably accommodates four guests in two bedrooms and one bathroom. It features a well-equipped kitchen, a private hot tub and sauna, a modern bathroom, and outdoor spaces perfect for relaxing. Guests can enjoy the convenience of a dedicated EV charger, e-bikes for exploring the area, and a range of amenities for a comfortable stay.
A Wave From It All! - Lake Condo - Sheboygan, WI
10 64 reviews
Sheboygan, WI
20/09 – 25/09
108 €/nighttotal: 540 € (5 )

A Wave From It All! - Lake Condo

1 4
apartment , Sheboygan
This ground floor apartment is conveniently located just a short walk, less than 1.6km, from the South Boardwalk and North Beach in Sheboygan, offering easy access to the city's attractions and scenic lakefront views. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a comfortable living area, and a keyless entry system. Guests can enjoy amenities such as a smart TV, free Wi-Fi, and a relaxing electric fireplace, while exploring the nearby historical sites and enjoying the beautiful lakefront views.
Sheboygan Falls: Rochester Ranch 3bed/1bath - Sheboygan, WI
10 2 reviews
Sheboygan, WI
10/08 – 13/08
197 €/nighttotal: 591 € (3 )

Sheboygan Falls: Rochester Ranch 3bed/1bath

3 2
apartment , Sheboygan Falls
This family-friendly flat in Sheboygan Falls is a short walk from Rochester Park, offering a blend of mid-century character and modern updates.
With three bedrooms, one bathroom, and a capacity for seven guests, this property includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden for your convenience.
Sheboygan Sunrise Beach Stay - Sheboygan, WI
10 6 reviews
Sheboygan, WI
20/09 – 25/09
199 €/nighttotal: 995 € (5 )

Sheboygan Sunrise Beach Stay

2 4
apartment , Sheboygan
This Sheboygan apartment, a first-floor condo in the Ellis Historical District, is situated steps from Lake Michigan and within easy walking distance of Sheboygan's restaurants, bars, and the Riverwalk, offering proximity to the John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts.
The two-bedroom, one-bathroom flat sleeps up to six guests, featuring a fully equipped kitchen, two queen bedrooms with TVs and internet access, a pull-out sofa bed, keyless entry, and free on-street parking.

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

Among the 223 accommodations in Sheboygan, WI, here are the 2 best apartments with a pool

Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
10 8 reviews
Sheboygan, WI
10/08 – 13/08
2348 €/nighttotal: 7044 € (3 )

Baronwood Oasis | Pool + Arcade Mega Estate

7 2
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.
Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
Sheboygan, WI
10/08 – 13/08
878 €/nighttotal: 2634 € (3 )

Luxury Pool Retreat-2 Acres-near Whistling Straits

1 2
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

Vintage Sheboygan - Sheboygan, WI
9.4 140 reviews
Sheboygan, WI
26/07 – 30/07
136 €/nighttotal: 544 € (4 )

Vintage Sheboygan

1 4
apartment , Sheboygan
This three-bedroom apartment in Sheboygan is located just 1.6 kilometres from the Lake Michigan beach and within walking distance of the 8th Street restaurants.
The apartment features a spacious living room, an eat-in kitchen with a separate butler's pantry, and a bathroom with a clawfoot tub shower enclosure, offering ample space for a comfortable stay.
Lake Michigan View Steps Beach - Sheboygan, WI
Sheboygan, WI
25/07 – 26/07
1629 €/nightfor 1 night

Lake Michigan View Steps Beach

1 2
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.
Blue Horizons Hideaway— Close To Downtown & Marina - Sheboygan, WI
10 1 review
Sheboygan, WI
06/08 – 09/08
213 €/nighttotal: 639 € (3 )

Blue Horizons Hideaway— Close To Downtown & Marina

1 2
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.
New Cozy Family Downtown Home W/ Yard -Photos Soon - Sheboygan, WI
Sheboygan, WI
06/08 – 09/08
207 €/nighttotal: 621 € (3 )

New Cozy Family Downtown Home W/ Yard -Photos Soon

1 2
apartment , Sheboygan
This city centre flat in Sheboygan is located 2.9 kilometres from North Point Park.
This pet-friendly accommodation offers space for seven guests and features a large, enclosed garden with a fire pit and barbecue, alongside an on-site playground for children.

Best pet-friendly Sheboygan, WI holiday apartments

Among the 223 accommodations in Sheboygan, WI, here are the 4 best pet friendly holiday apartments

Black River Retreat\neclectic-unique-intriguing - Sheboygan, WI
Sheboygan, WI
10/08 – 13/08
322 €/nighttotal: 966 € (3 )

Black River Retreat\neclectic-unique-intriguing

3 2
apartment , Sheboygan
This three-bedroom Sheboygan holiday home, situated in the Black River neighbourhood, is minutes from downtown Sheboygan, Kohler's beaches and parks, and offers easy access to Road America.
The property features a spacious layout accommodating seven guests, boasting two bathrooms, a dedicated children's play area, an indoor fireplace, and a large garden exceeding 0.4 hectares, plus unique features such as a pinball machine and record player.
Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit - Sheboygan, WI
10 7 reviews
Sheboygan, WI
26/07 – 30/07
361 €/nighttotal: 1444 € (4 )

Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit

3 4
apartment , Sheboygan
This three-bedroom Sheboygan holiday home is situated near Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park.
Offering a mid-century modern design, this self-catering property sleeps six, includes a fully equipped kitchen with basic staples, a fenced backyard, a games room with a foosball table, and amenities such as shampoo, conditioner, and dishwasher tablets.
*Front Porch, Fenced In Backyard- Petswelcome* - Sheboygan, WI
9.9 146 reviews
Sheboygan, WI
20/09 – 25/09
192 €/nighttotal: 960 € (5 )

*Front Porch, Fenced In Backyard- Petswelcome*

1 4
apartment , Sheboygan
This apartment is located in a bohemian district of Sheboygan, just a 10-minute drive from Whistling Straits/Irish golf course and the Kohler Water Spa, and a short walk from the town centre. It has excellent user, location and cleanliness ratings.
The self-catering property has 4 bedrooms, 1 bathroom and a floor area of 130 square metres, accommodating up to 5 guests. It offers a range of amenities, including a fully equipped kitchen, a garden, a spa, a jacuzzi, parking, and a variety of outdoor and beach amenities.
Dog Friendly Cozy Cottage Rental On Lake Michigan! - Sheboygan, WI
9.7 220 reviews
Sheboygan, WI
26/07 – 30/07
330 €/nighttotal: 1320 € (4 )

Dog Friendly Cozy Cottage Rental On Lake Michigan!

1 4
apartment , Sheboygan
This two-bedroom house in Sheboygan, Wisconsin, offers stunning panoramic views of Lake Michigan and is located within a short drive of Kohler, Whistling Straits and Road America.
The property features a fully equipped kitchen, a cosy living room with a wood-burning stove, a private garage and a patio with a gas grill and fire pit, perfect for enjoying the outdoors.
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