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Sheboygan, WI vacation rentals
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Best Vacation rentals and Airbnb offers in Sheboygan, WI

Best family friendly Sheboygan, WI vacation rentals

Among the 274 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals

Breezy Condo W/ Fireplace & Balconies - Sheboygan, WI
9.9 148 reviews
Sheboygan, WI
08/06 – 08/09
$545/nighttotal: $1635 (3 )

Breezy Condo W/ Fireplace & Balconies

2 2
apartment , Sheboygan
This Sheboygan apartment is located just a short walk from the beach, downtown, and the River Boardwalk, offering easy access to shops, restaurants, and attractions. This property has excellent ratings for location, cleanliness, and user experience.
The second-floor apartment sleeps up to 5 guests and includes 2 bedrooms and 1 bathroom. Guests can enjoy a fully equipped kitchen, a garden, air conditioning, internet access, a fireplace, a Roku TV, and parking.
The Garden | Sheboygan 2 Br/1ba, Pet Friendly - Sheboygan, WI
9.7 101 reviews
Sheboygan, WI
07/24 – 07/26
$294/nighttotal: $588 (2 )

The Garden | Sheboygan 2 Br/1ba, Pet Friendly

2 2
apartment , Sheboygan
The Garden apartment is located in downtown Sheboygan, just three blocks from Lake Michigan, offering easy access to the city's attractions and the beautiful lakefront. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience. The apartment features two bedrooms and one bathroom, comfortably accommodating up to four guests. The well-equipped kitchen includes a fridge, freezer, microwave oven, and dishwasher, while amenities like air conditioning, parking, internet, and pet-friendly policies ensure a comfortable and convenient stay.
2 Mi To Dtwn: Studio Suite In Sheboygan - Sheboygan, WI
10 1 review
Sheboygan, WI
08/06 – 08/09
$231/nighttotal: $693 (3 )

2 Mi To Dtwn: Studio Suite In Sheboygan

1 2
studio , Sheboygan
This Sheboygan studio apartment is conveniently located near downtown, approximately 2 miles from Deland Park and Vollrath Park, offering easy access to Lake Michigan and recreational activities.
The 620-square-foot unit features a queen-size bed, a fully equipped kitchen with a fridge and microwave, free Wi-Fi, keyless entry, a private balcony, and accommodates up to two guests, with pet-friendly options available for an additional fee.
Central Located. Seconds From The Highway To Get To Kohler, And Elkhart Lake - Sheboygan, WI
10 3 reviews
Sheboygan, WI
07/26 – 07/30
$972/nighttotal: $3888 (4 )

Central Located. Seconds From The Highway To Get To Kohler, And Elkhart Lake

4 4
apartment , Sheboygan
This Sheboygan vacation home is conveniently located near both the hospital and Lake Michigan, offering easy access to medical facilities and the beautiful shoreline. It is highly rated by previous guests, earning an "excellent" user rating. This spacious 4-bedroom, 3-bathroom home comfortably accommodates up to 14 guests. The home comes equipped with a fully stocked kitchen, a comfortable living area, and a relaxing patio, perfect for enjoying outdoor meals and soaking up the Sheboygan sunshine.

Best Sheboygan, WI vacation rentals with a pool

Among the 274 accommodations in Sheboygan, WI, here are the 2 best rentals with a pool

Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
Sheboygan, WI
07/26 – 07/30
$1169/nighttotal: $4676 (4 )

Luxury Pool Retreat-2 Acres-near Whistling Straits

1 4
apartment , Sheboygan
This 4-bedroom, 4-bathroom house is situated on 2 private acres in Sheboygan, offering 12-guest capacity and convenient access to Whistling Straits Golf Course (8 miles), Road America (20 miles), and Lake Michigan.
This family-friendly rental features a heated in-ground pool (May-September), a large, fully equipped kitchen, multiple indoor living areas, and air conditioning, making it ideal for golf trips and family getaways.
Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
10 8 reviews
Sheboygan, WI
08/10 – 08/13
$2714/nighttotal: $8142 (3 )

Baronwood Oasis | Pool + Arcade Mega Estate

7 2
apartment , Sheboygan
This 10,500-square-foot luxury estate in Sheboygan, Wisconsin, is minutes from the Whistling Straits golf course, Kohler Co. amenities, and Lake Michigan.
This seven-bedroom, seven-bathroom home sleeps twenty guests and boasts an indoor pool and spa, a private arcade, a gourmet chef's kitchen, and concierge services including private chefs and massage therapists.

Frequently Asked Questions about vacation rentals in Sheboygan, WI

  • What are the must-see sights in Sheboygan, Wisconsin?

    Sheboygan has a lot to offer! The Sheboygan Maritime Museum is a great place to learn about the city's rich history as a shipbuilding and fishing center. The John Michael Kohler Arts Center showcases contemporary art in a stunning setting. For a taste of local history and architecture, stroll along the historic Eighth Street business district. Finally, don't miss the beautiful Sheboygan Riverwalk, perfect for a relaxing walk.
  • What are the best Airbnb and vacation rentals in Sheboygan, WI?

  • Are there unique natural phenomena in Sheboygan, Wisconsin?

    While Sheboygan doesn't have dramatic geological features, its location on Lake Michigan provides beautiful natural scenery. The lake itself offers stunning sunsets and opportunities for swimming, boating, and fishing. The shoreline provides nice walking paths and views. Kohler-Andrae State Park, just south of Sheboygan, offers beaches, dunes, and diverse birdlife.
  • What are the most popular Airbnbs in Sheboygan, WI?

    Among the Airbnbs in Sheboygan, WI, Cozy Sheboygan Upper, Carriage House Sheboygan - Garage Parking Included and Downtown Walk-up are the most popular ones.

  • What essentials should you bring along for a trip to Sheboygan, Wisconsin?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Depending on the season, you'll want layers of clothing, including a light jacket or sweater even in summer. Sunscreen and a hat are essential, especially during the warmer months. Don't forget your swimsuit if you plan on enjoying Lake Michigan!
  • What are the best vacation rentals with a pool in Sheboygan, WI?

  • What famous events or festivals are happening in Sheboygan, Wisconsin?

    Sheboygan's biggest event is probably the Bratwurst Festival, a massive celebration of, you guessed it, bratwurst! It's a multi-day event with live music, food, and family-friendly activities. The city also hosts various smaller events throughout the year, so checking the local event calendar closer to your travel dates is a good idea.
  • What are the best rentals for families and kids in Sheboygan, WI?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Sheboygan, Wisconsin?

    A daily budget of $150-$300 per person should cover a comfortable trip to Sheboygan. This is just an estimate, and costs can vary depending on your accommodation choices, dining preferences, and activities. Budget-friendly options are available, and you can easily adjust your spending to fit your needs.
  • What are the best rentals or Airbnbs with a jacuzzi in Sheboygan, WI?

  • Where can you find the best restaurants serving local dishes in Sheboygan, Wisconsin, and what are the must-try specialties?

    Sheboygan is known for its German heritage, so you'll find many restaurants serving traditional German fare. The local bratwurst is a must-try! Several restaurants along Eighth Street offer delicious meals. For a broader range of options, explore the city's diverse culinary scene; you'll find everything from seafood to Italian cuisine.
  • What are some less-famous attractions in Sheboygan, Wisconsin that are worth the visit?

    The Sheboygan County Historical Museum offers a deeper dive into the area's history. The Blue Harbor Resort and Spa, while known for its amenities, also has beautiful grounds worth exploring. Consider a visit to the local farmers' markets for a taste of the region's fresh produce and local goods.
  • What are the best activities for engaging with locals and understanding their culture in Sheboygan, Wisconsin?

    Attending the Bratwurst Festival is a great way to experience Sheboygan's community spirit. Visiting local shops and businesses in the historic Eighth Street district allows you to interact with residents. Consider attending a local event or farmers' market to get a feel for everyday life.
  • What unique natural landscapes and terrain features can travelers explore in Sheboygan, Wisconsin?

    Sheboygan's most striking natural feature is its Lake Michigan shoreline, with its sandy beaches and the impressive dunes of Kohler-Andrae State Park. The Sheboygan River also offers scenic views and opportunities for kayaking or paddleboarding.
  • How many days are ideal for visiting Sheboygan, Wisconsin, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Sheboygan at a relaxed pace. A possible itinerary could include a day exploring the downtown area, including the Maritime Museum and Arts Center; a day at Kohler-Andrae State Park; and a day enjoying the Riverwalk and perhaps a local brewery.

Nearby regions

Best Sheboygan, WI vacation rentals with a balcony

The Links! - Luxury Golf Retreat With Golf Simulator - Sheboygan, WI
10 8 reviews
Sheboygan, WI
08/06 – 08/09
$1015/nighttotal: $3045 (3 )

The Links! - Luxury Golf Retreat With Golf Simulator

4 2
apartment , Sheboygan
This Sheboygan apartment rental, conveniently located near Blackwolf Run golf course and the Above & Beyond Children's Museum, offers easy access to local attractions and shopping at Deer Trace Mall and the Farmers Market.
The spacious four-bedroom, three-bathroom dwelling comfortably sleeps eight guests and features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, plus a terrace, parking, and high-speed internet access.
Beach Lake House Walking Disance To Lake Close To Downtown\n & South Pier\n4br 2ba - Sheboygan, WI
9.2 9 reviews
Sheboygan, WI
08/10 – 08/13
$615/nighttotal: $1845 (3 )

Beach Lake House Walking Disance To Lake Close To Downtown\n & South Pier\n4br 2ba

4 2
apartment , Sheboygan
This family-friendly apartment is located in downtown Sheboygan, 5 minutes by foot from St. Peter Claver Parish and 8 minutes by foot from Lake Michigan.
This 1500 square foot vacation home accommodates 12 guests with 4 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, free Wi-Fi, and a garden with a fire pit and barbecue.
Fully Renovated, Updated, And High-end Finished 5 Bedroom Facing The Marina! - Sheboygan, WI
10 4 reviews
Sheboygan, WI
09/20 – 09/25
$550/nighttotal: $2750 (5 )

Fully Renovated, Updated, And High-end Finished 5 Bedroom Facing The Marina!

5 4
apartment , Sheboygan
This Sheboygan waterfront rental, situated in the Ellis Historical District, is just one block from the beach and near the Above & Beyond Children's Museum and Blackwolf Run.
This five-bedroom, three-bathroom home sleeps twelve and boasts a fully renovated interior with high-end finishes, a private garden, a fitness center, extensive entertainment options including a movie room and basement arcade, and a fully equipped kitchen perfect for group dining.
3 Blocks From Lake Walk To Lake, Guest House 1 Bdrm Full Bath 4 Min To Downtown - Sheboygan, WI
9.8 15 reviews
Sheboygan, WI
08/06 – 08/09
$358/nighttotal: $1074 (3 )

3 Blocks From Lake Walk To Lake, Guest House 1 Bdrm Full Bath 4 Min To Downtown

1 2
apartment , Sheboygan
This downtown Sheboygan apartment is located a short walk from St. Peter Claver Parish and 0.4 miles from Lake Michigan, offering proximity to local attractions and outdoor recreation.
This family-friendly vacation rental accommodates 2 guests with 1 bedroom and 1 bathroom, featuring a kitchen with a fridge and microwave, air conditioning, a private terrace with a fire pit, and on-site parking.

Neighborhoods and points of interest in Sheboygan, WI

Best Sheboygan, WI vacation rentals with parking

The Perfect Location! - Sheboygan, WI
9.8 53 reviews
Sheboygan, WI
09/20 – 09/25
$223/nighttotal: $1115 (5 )

The Perfect Location!

3 4
apartment , Sheboygan
This Sheboygan apartment is located in a historic neighborhood, just three blocks from downtown and two blocks from Lake Michigan. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy a fully equipped kitchen, a washer and dryer, free parking, a small yard, and a front patio, plus easy access to the beach, downtown shops, restaurants, and local attractions.
Boutique Wellness Retreat - Hot Tub And Fireplace - Sheboygan, WI
10 266 reviews
Sheboygan, WI
07/24 – 07/26
$559/nighttotal: $1118 (2 )

Boutique Wellness Retreat - Hot Tub And Fireplace

1 2
apartment , Sheboygan
This charming house is located in a peaceful Sheboygan neighborhood, just blocks from Lake Michigan and a short drive to Whistling Straits. It boasts excellent user, location, and cleanliness ratings. This two-bedroom, one-bathroom house can accommodate up to four guests. Enjoy the modern amenities, including a hot tub, sauna, a fully equipped kitchen, and a beautiful patio for al fresco dining.
Beachside Condo Downtown With Lake Michigan Views - Sheboygan, WI
10 29 reviews
Sheboygan, WI
08/10 – 08/13
$493/nighttotal: $1479 (3 )

Beachside Condo Downtown With Lake Michigan Views

2 2
apartment , Sheboygan
This Sheboygan waterfront condo, located less than 200 feet from the beach near Blue Harbor Resort and within walking distance of downtown, offers direct lakefront access with stunning views.
The 800-square-foot apartment features two bedrooms, one bathroom, sleeps four, and includes a fully stocked kitchen, in-unit laundry, high-speed Wi-Fi, and access to beach chairs, towels, and toys.
Beachside, Chefs Kitchen, High-end Everything - Sheboygan, WI
10 12 reviews
Sheboygan, WI
08/10 – 08/13
$923/nighttotal: $2769 (3 )

Beachside, Chefs Kitchen, High-end Everything

3 2
apartment , Sheboygan
This Sheboygan vacation home, located in the Ellis Historical District, is within walking distance of Lake Michigan, the riverfront, downtown, and the North Pierhead Lighthouse.
The 1,880-square-foot house features three bedrooms, three bathrooms, sleeps six, and includes amenities such as bicycles, a gas grill, and a well-equipped kitchen with a six-burner gas cooktop; nearby attractions include the John Michael Kohler Arts Center and the Stefanie H. Weill Center for the Performing Arts.
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