Find short term rentals in Sheboygan, WI at the best prices

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Sheboygan, WI short term rentals
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Best Short term and Weekly rentals in Sheboygan, WI

Best family friendly Sheboygan, WI Short term rentals

Among the 335 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals

Boutique Wellness Retreat - Hot Tub And Fireplace - Sheboygan, WI
9.9 275 reviews

Boutique Wellness Retreat - Hot Tub And Fireplace

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.
Recombobulation Station-in The Heart Of Sheboygan! - Sheboygan, WI
10 98 reviews

Recombobulation Station-in The Heart Of Sheboygan!

apartment, Sheboygan
This charming upper-floor flat is situated in Sheboygan, just a short walk from both the beach and the town centre, making it ideal for exploring the area's natural beauty and cultural attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The property offers two bedrooms and one bathroom, comfortably accommodating up to five guests. It comes equipped with a fully-equipped kitchen, including a fridge, freezer, microwave, and dishwasher, ensuring a comfortable and convenient stay. Guests can also enjoy a garden, parking, and fast Wi-Fi, as well as the added bonus of a local recommendations guide from the hosts.
2 Bed/2 Bath Townhouse On A Quiet Cul De Sac With Backyard Views And A Hot Tub - Sheboygan, WI
10 193 reviews

2 Bed/2 Bath Townhouse On A Quiet Cul De Sac With Backyard Views And A Hot Tub

apartment, Sheboygan
This family-friendly holiday home is located in Sheboygan, just 5km from Lake Michigan and within 10km of attractions such as the Blue Harbor Resort & Conference Center Water Park and Bookworm Gardens. The property has received excellent user ratings, making it a popular choice for travellers.
The two-bedroom house spans 136 square metres and provides a comfortable and spacious living environment. It offers a range of amenities including a fully equipped kitchen, a fireplace, a Jacuzzi, a terrace, a garden, and parking.
A Glorious Getaway Sheboygan - Lux Lake Condo - Sheboygan, WI
9.6 11 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.

Best Sheboygan, WI lodging with a balcony

Beachside Condo Downtown With Lake Michigan Views - Sheboygan, WI
10 30 reviews

Beachside Condo Downtown With Lake Michigan Views

apartment, Sheboygan
This Sheboygan lakeside apartment, less than 0.2 kilometres from the beach and close to Blue Harbor Resort, offers easy access to the downtown area and its shops, restaurants, and art venues.
The 74 square metre property features two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, washer/dryer, private decks with Lake Michigan views, and off-street parking; nearby attractions include Whistling Straits (15 minutes' drive) and Road America (25 minutes' drive).
Coastal 3-br Lower Near Lake Mi And Downtown Sheboygan - Sheboygan, WI
9.4 12 reviews

Coastal 3-br Lower Near Lake Mi And Downtown Sheboygan

apartment, Sheboygan
This three-bedroom apartment is conveniently located near Sheboygan's city centre, offering easy access to Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park.
The self-catering property sleeps five guests and includes a fully equipped kitchen, family-friendly amenities such as a travel cot and highchair, a smart TV with streaming services, and an enclosed porch; board games and puzzles are also provided.
Private Guest Bedroom-1w West Room - Close To Lake Michigan - Sheboygan, WI
9.9 25 reviews

Private Guest Bedroom-1w West Room - Close To Lake Michigan

B&B, Sheboygan
This charming bed and breakfast is located in a quiet residential area of Sheboygan, just 3 kilometres from the Children's Museum and within easy reach of Lake Michigan. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The property features a comfortable bedroom, two bathrooms, and a fully equipped kitchen, offering a total floor area of 9 square metres and accommodating up to two guests. Enjoy the peaceful courtyard views, relax in the Jacuzzi, and make the most of the outdoor fireplace, the tennis court, and the rental services for bicycles and cars.
Boutique Gallery House - Stay Inside A Work Of Art - Sheboygan, WI
10 81 reviews

Boutique Gallery House - Stay Inside A Work Of Art

apartment, Sheboygan
This Sheboygan guesthouse enjoys a prime downtown location, within easy walking distance of the farmers market, shops, restaurants, the Kohler Art Center, and the beach, with Kohler-Andrae State Park a short 11km drive away.
The newly renovated 1904 home offers three bedrooms, sleeping up to six guests, boasting a master suite, two queen bedrooms, a den, modern amenities including air conditioning and off-street parking, plus an art gallery showcasing regional artists.

Frequently Asked Questions about short term rentals in Sheboygan, WI

  • What attractions should you visit during a week-long stay in Sheboygan, Wisconsin?

    A week in Sheboygan offers plenty to explore! Start with the Sheboygan Maritime Museum, showcasing the city's rich shipbuilding history. Then, head to the John Michael Kohler Arts Center, known for its impressive collection and rotating exhibits. A stroll along the Sheboygan Riverwalk is a must, offering beautiful views. Consider visiting the Blue Harbor Resort & Spa for some relaxation. For outdoor activities, explore the trails at Evergreen Park or Kohler-Andrae State Park. Don't forget to check out the local shops and boutiques in downtown Sheboygan.
  • What are the best short term rentals in Sheboygan, WI?

    Among the short term rentals in Sheboygan, WI, Cozy Sheboygan Upper, Downtown Walk-up and Seagull Beach Guest House - Lake Michigan Cottage On Private Beach are the most popular ones.

  • What attractions should you visit when you spend a month in Sheboygan, Wisconsin?

    With a month, you can delve deeper into Sheboygan's offerings. Beyond the attractions mentioned for a week-long trip, explore the local breweries, such as 3 Sheeps Brewing Company and Sheboygan Brewing Company. Take day trips to nearby towns like Kohler, famous for its Kohler Company and golf courses. Visit the Wisconsin Cheese Mart for a taste of Wisconsin's dairy heritage. Spend time exploring the beaches along Lake Michigan, like those at Kohler-Andrae State Park. Consider attending a performance at the Weill Center for the Performing Arts. You could also explore the many parks and nature trails in the surrounding area, such as the Oostburg State Park.
  • What are the best short term rentals with a pool in Sheboygan, WI?

  • Can visitors to Sheboygan, Wisconsin witness any unique natural cycles, like cherry blossom season or autumn colors?

    While Sheboygan doesn't have widespread cherry blossoms like some areas, the autumn colors in the parks and surrounding areas are quite stunning, typically peaking in October. Kohler-Andrae State Park and Evergreen Park are excellent spots for viewing the fall foliage.
  • What are the best short term rentals with a jacuzzi in Sheboygan, WI?

  • What are the most meaningful ways to engage with locals and discover the culture in Sheboygan, Wisconsin?

    To connect with locals, visit the farmers' markets during the summer months, where you can interact with vendors and sample local produce. Attend events at the Weill Center for the Performing Arts or check out local festivals. Exploring the downtown area and chatting with shop owners is another great way to engage with the community. Consider visiting local restaurants and trying the unique dishes. Sheboygan has a strong German heritage, so exploring that aspect of the culture could be particularly rewarding.
  • What are the best short term rentals for families and kids in Sheboygan, WI?

  • Are there any distinctive cultural activities or hands-on workshops in Sheboygan, Wisconsin?

    The John Michael Kohler Arts Center often hosts workshops and classes related to art and creativity. Check their website for current offerings. Many local breweries offer tours and tastings. You might also find pottery classes or other craft workshops at local studios, although availability varies.
  • What are some secret spots or hidden treasures to visit in Sheboygan, Wisconsin?

    One relatively undiscovered gem is the Bookworm Gardens, a unique outdoor children's book-themed garden. Exploring the quieter residential streets near the lake can reveal charming architecture and hidden parks. The local beaches outside of the main areas can offer a more secluded experience. Look for smaller, family-owned shops and restaurants off the main streets for a more authentic Sheboygan experience.
  • What should not be left out of your suitcase if you are going to Sheboygan, Wisconsin?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Layers are essential, as the weather can be unpredictable. Don't forget swimwear if you plan on visiting the beaches. Sunscreen and insect repellent are also recommended, especially during the warmer months.
  • What are the most popular festivals in Sheboygan, Wisconsin?

    Sheboygan has several festivals throughout the year. The Brat Days festival is a popular event, celebrating bratwurst. The Wisconsin Cheese Festival (though not exclusively Sheboygan) often draws large crowds. There are also smaller, local events throughout the year, best checked through the local event listings closer to your travel dates.
  • Where should you try the best local food in Sheboygan, Wisconsin?

    For a taste of Sheboygan's culinary scene, try restaurants like the 8th Street Ale Haus for pub fare and local brews. The Black Pig is known for its upscale dining experience. Many smaller eateries offer delicious and authentic Wisconsin cuisine. Don't forget to try some local cheese and bratwurst at various locations throughout the city.

Nearby regions

Best Sheboygan, WI lodging with a kitchen

Grammys House In A Quiet And Convenient Location - Sheboygan, WI
9.9 86 reviews

Grammys House In A Quiet And Convenient Location

apartment, Sheboygan
This family-friendly four-bedroom house in central Sheboygan offers convenient access to local attractions and amenities.
The property boasts a finished basement with office space, play area, and workout equipment, comfortably accommodating eight guests with a fully equipped kitchen and a newly enclosed toilet; a 10% discount is available for returning guests.
Unmatched Location, Views, & Style. Welcome Home! - Sheboygan, WI
10 74 reviews

Unmatched Location, Views, & Style. Welcome Home!

B&B, Sheboygan
This newly built three-bedroom, three-bathroom house in Sheboygan, Wisconsin, is situated at the mouth of the Sheboygan River where it meets Lake Michigan, steps from the Sheboygan boardwalk and marina.
The property boasts a unique sailboat-shaped deck with Lake Michigan views, an open-plan kitchen, dining and living area, on-site laundry, and sleeps six guests comfortably, offering easy access to Sheboygan's downtown restaurants, shops and attractions.
Feel At Home In This 3 Bedroom, 2 Bath Home. - Sheboygan, WI
9.9 30 reviews

Feel At Home In This 3 Bedroom, 2 Bath Home.

apartment, Sheboygan
This three-bedroom house is located in Sheboygan, just 7 km from Kohler Andrae State Park and a short distance from Lake Michigan beaches. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The house has a split bedroom floor plan, ideal for families or groups of up to six guests. The spacious kitchen, complete with a dishwasher, laundry room, and a private fenced backyard with a large deck, dining area, gazebo and barbeque grill, provides ample space for both relaxation and entertainment.
Vacay Vibes - Sheboygan, WI
10 23 reviews

Vacay Vibes

apartment, Sheboygan
This three-bedroom, two-bathroom flat in Sheboygan offers a residential street location with easy walking access to dining, shopping, and entertainment, situated just 1.6 kilometres from the beach.
This pet-friendly accommodation for six guests boasts a fully equipped kitchen, air conditioning, a garden with a fire pit, and keyless entry, providing a comfortable base for exploring Sheboygan.

Best Sheboygan, WI lodging with laundry available

Storybook 2-bedroom Apartment 1mi From Lake Michigan - Sheboygan, WI
10 3 reviews

Storybook 2-bedroom Apartment 1mi From Lake Michigan

apartment, Sheboygan
This creatively decorated, private lower-level flat, named 'Fox & Folly', offers a unique storybook adventure in Sheboygan, located in a peaceful neighbourhood just 1.6 kilometres from South Beach, North Beach on Lake Michigan, and the Sheboygan Pier, with Bookworm Gardens also nearby.
This two-bedroom, one-bathroom apartment accommodates up to five guests with a king-size bed in the master, a full-over-twin bunk in the second bedroom, a fully stocked kitchen featuring a Keurig coffee bar and reverse osmosis filtered water, air conditioning, on-site parking, and a private fenced backyard with a fire pit, plus exclusive access to a shared basement game room.
Pet Friendly, Freshly Renovated, 5 Minute Walk To Beach In The Heart Of The City - Sheboygan, WI
9.8 32 reviews

Pet Friendly, Freshly Renovated, 5 Minute Walk To Beach In The Heart Of The City

apartment, Sheboygan
This four-bedroom, two-bathroom holiday home is situated in Sheboygan's North Side, less than 1.6km from the Above & Beyond Children's Museum and Lake Michigan, and a short drive from the Stefanie H. Weill Center for the Performing Arts.
Sleeping up to 11 guests, the property boasts a fully equipped kitchen, laundry facilities, a smart TV, outdoor barbecue grills, and is within easy reach of North Side Municipal Beach; pets are welcome.
Close To Lake Michigan And Downtown Sheboygan - Sheboygan, WI
10 90 reviews

Close To Lake Michigan And Downtown Sheboygan

apartment, Sheboygan
This four-bedroom house is located on the North Side of Sheboygan, just one block from Lake Michigan and a short walk from the harbour, the YMCA, and the city centre. The property has received excellent ratings for its location, cleanliness and user experience.
The house can accommodate up to eight guests and features a fully equipped kitchen, a private garden, and parking. The property is also conveniently located near a trolley stop and is a short drive from popular golfing destinations and the Road America motorsports racetrack.
King/queen Upper Unit Sleeps 5 Near Downtown - Sheboygan, WI
10 7 reviews

King/queen Upper Unit Sleeps 5 Near Downtown

apartment, Sheboygan
This newly renovated upper-floor flat in Sheboygan is situated just over 1.6 kilometres from the town centre and the beach, providing convenient access to waterfront parks, dining, and shops.
This 3-bedroom, 1-bathroom flat accommodates up to 5 guests and features a fully equipped kitchen, central air conditioning, free on-site parking for two vehicles, and complimentary use of a basement washer and dryer.
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