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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

Black River Retreat - Sheboygan, WI
9.6 38 reviews
Sheboygan, WI
09/20 – 09/25
$242/nighttotal: $1210 (5 )

Black River Retreat

1 4
apartment , Sheboygan
This four-bedroom Cape Cod-style house in Sheboygan's Black River neighborhood is minutes from downtown Sheboygan, Kohler-Andrae State Park, and Lakeview Park.
This family-friendly home, boasting a large yard over an acre, sleeps six and features two bathrooms, a full kitchen with fridge and microwave, air conditioning, Wi-Fi, a wood-burning fireplace, a kids' zone, and an eclectic study with vintage furnishings.
Clean, Comfy Stay Near Parks, Downtown & Lake! - Sheboygan, WI
10 38 reviews
Sheboygan, WI
08/10 – 08/13
$130/nighttotal: $390 (3 )

Clean, Comfy Stay Near Parks, Downtown & Lake!

1 2
apartment , Sheboygan
This Sheboygan apartment rental is conveniently located near Interstate 43, directly across from Shaw Family Park, and within walking distance of a Starbucks.
The two-bedroom, one-bathroom unit sleeps four guests and features a kitchen, air conditioning, parking, internet access, and proximity to Sheboygan's beachfront, Fireman's Park, and renowned golf courses like Whistling Straits.
New Riverfront Loft - Fantastic Location W/stunning Views - On The Boardwalk! - Sheboygan, WI
10 9 reviews
Sheboygan, WI
08/10 – 08/13
$461/nighttotal: $1383 (3 )

New Riverfront Loft - Fantastic Location W/stunning Views - On The Boardwalk!

1 2
apartment , Sheboygan
This waterfront loft offers a prime location in Sheboygan's city center, situated directly on the boardwalk where the river meets Lake Michigan, providing immediate access to boutique shops, restaurants, and charter fishing.
This family-friendly apartment spans 1610 square feet, accommodating up to six guests with a king bedroom, a queen sleeper sofa, a kids' nook with a queen floor bed, a fully equipped kitchen, an electric fireplace, a 65-inch TV, and a 12 ft shuffleboard.
Walk To Beach & Pier | Fully-loaded Kitchen - Sheboygan, WI
10 2 reviews
Sheboygan, WI
07/03 – 07/06
$1322/nighttotal: $3966 (3 )

Walk To Beach & Pier | Fully-loaded Kitchen

5 2
apartment , Sheboygan
This 5-bedroom, 4-bathroom vacation home in Sheboygan is a short walk to Lake Michigan's public beach and the North Pier, and within a short drive of Kohler golf courses and Road America.
This spacious rental accommodates up to 11 guests with a fully equipped kitchen, dedicated office space, and a fireplace, offering convenient access to local dining, shopping, and a seasonal farmers market.

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
08/10 – 08/13
$1015/nighttotal: $3045 (3 )

Luxury Pool Retreat-2 Acres-near Whistling Straits

1 2
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 Beach Town Bungalow - Sheboygan, WI
Sheboygan, WI
07/03 – 07/06
$343/nighttotal: $1029 (3 )

The Beach Town Bungalow

2 2
apartment , Sheboygan
This apartment in Sheboygan is a 10-minute walk from the Sheboygan County Historical Museum and a 5-minute drive from Lake Michigan.
This 2-bedroom, 1-bathroom rental accommodates up to 5 guests and offers amenities such as internet, air conditioning, a kitchen with a fridge and microwave, a balcony, garden, and on-site parking.
Lake Michigan Home With Gorgeous Views, Great Spot For Family Or Golf Retreat - Sheboygan, WI
9.9 275 reviews
Sheboygan, WI
09/20 – 09/25
$793/nighttotal: $3965 (5 )

Lake Michigan Home With Gorgeous Views, Great Spot For Family Or Golf Retreat

5 4
apartment , Sheboygan
This lakefront house is located in a quiet residential neighborhood in Sheboygan, just minutes from downtown, Kohler, and the beaches and dunes of Kohler Andrae State Park. The property has received excellent ratings for user experience, location, and cleanliness.
The 2,800 square foot house has 5 bedrooms, 3 bathrooms, and can accommodate up to 14 guests. It offers a fully equipped kitchen, a spacious living area, a relaxing spa, a backyard with a fire pit and grill, and a variety of other amenities for a comfortable and enjoyable stay.
Malibu Of The Midwest Condo Steps From The Lake - Sheboygan, WI
10 110 reviews
Sheboygan, WI
09/20 – 09/25
$311/nighttotal: $1555 (5 )

Malibu Of The Midwest Condo Steps From The Lake

2 4
apartment , Sheboygan
This Sheboygan apartment is located right across the street from Lake Michigan's sandy beach and a short walk from the riverwalk with cafes, pubs, and shops. The apartment has received excellent ratings for location, cleanliness, and user experience.
The 1400 square foot apartment sleeps up to 6 guests and includes 2 bedrooms and 2 bathrooms. Enjoy amenities such as a fully equipped kitchen, a relaxing balcony, a free washer and dryer, a Roku stick, free WiFi, and a garden.
Beachside Condo Downtown With Lake Michigan Views - Sheboygan, WI
10 29 reviews
Sheboygan, WI
09/20 – 09/25
$328/nighttotal: $1640 (5 )

Beachside Condo Downtown With Lake Michigan Views

2 4
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.

Neighborhoods and points of interest in Sheboygan, WI

Best Sheboygan, WI vacation rentals with parking

Eclectic Spacious 3 Br Home Near Lake Mi W/ Fire Pit - Sheboygan, WI
10 7 reviews
Sheboygan, WI
09/18 – 09/25
$271/nighttotal: $1897 (7 )

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

3 4
apartment , Sheboygan
This Sheboygan rental is conveniently located near Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park, offering easy access to Sheboygan's premier attractions. This three-bedroom, one-bathroom home sleeps six, features a fully equipped kitchen with basic staples, a fenced backyard, a game room with a foosball table, and provides amenities like a pack-n-play and highchair for families.
King Bed Near Lake W/ Fire Pit & Pack N Play - Sheboygan, WI
9.9 155 reviews
Sheboygan, WI
08/10 – 08/13
$214/nighttotal: $642 (3 )

King Bed Near Lake W/ Fire Pit & Pack N Play

1 2
apartment , Sheboygan
This three-bedroom Sheboygan duplex, near Lake Michigan, offers easy access to Whistling Straits and Kohler-Andrae State Park.
The 3-bedroom rental boasts a fully equipped kitchen, private backyard with fire pit, keyless entry, and accommodates up to five guests with amenities including a pack 'n play and highchair.
Vintage Sheboygan - Sheboygan, WI
9.4 140 reviews
Sheboygan, WI
07/26 – 07/30
$157/nighttotal: $628 (4 )

Vintage Sheboygan

1 4
apartment , Sheboygan
This Sheboygan apartment is conveniently located just 10 blocks from Lake Michigan beach and within walking distance of the restaurants on 8th Street, providing easy access to the city's main attractions.
The 3-bedroom, 1-bathroom apartment features a well-equipped eat-in kitchen with a separate butler's pantry, a spacious living room, a clawfoot tub, and an outdoor space for relaxation.
Coastal Comfort & Golfers' Paradise In Sheboygan! - Sheboygan, WI
9.5 35 reviews
Sheboygan, WI
09/18 – 09/25
$275/nighttotal: $1925 (7 )

Coastal Comfort & Golfers' Paradise In Sheboygan!

3 4
house , Sheboygan
This Sheboygan vacation home is conveniently located within walking distance of North Side Municipal Beach and a short drive from South Side Municipal Beach, offering easy access to the beautiful Lake Michigan shoreline. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 3-bedroom, 2-bathroom rental comfortably accommodates up to 6 guests in its 1000 square feet of space. The house provides modern amenities like air conditioning, a fully equipped kitchen, free Wi-Fi, and comfortable bedding, making it perfect for families or groups looking for a relaxing getaway.
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