Compare best Airbnb in Sheboygan, WI from 100+ providers!

387 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Sheboygan, WI vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Sheboygan, WI

Best family friendly Sheboygan, WI vacation rentals

Among the 387 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals

Newly Renovated Lake Michigan Bungalow - Sheboygan, WI
9.4 22 reviews

Newly Renovated Lake Michigan Bungalow

apartment, Sheboygan
This newly renovated home is just two blocks from Lake Michigan in Sheboygan, within walking distance of the Marina, downtown restaurants, shops, and the Riverfront. The home has received excellent ratings for location, cleanliness, and user experience.
This vacation rental has two bedrooms and two bathrooms, comfortably accommodating up to eight guests. The home offers a fully equipped kitchen, central air conditioning, a washer and dryer, WiFi, and a spacious deck with lake views.
4b-2ba Home 3 Blocks From The Lake 10 To 12 Pp - Sheboygan, WI
9.8 32 reviews

4b-2ba Home 3 Blocks From The Lake 10 To 12 Pp

apartment, Sheboygan
This Sheboygan lakefront home, a 10-minute walk from St. Peter Claver Parish and under a mile from Blue Harbor Resort's water park, offers stunning Lake Michigan views.
This 1,500-square-foot vacation rental boasts four bedrooms, two bathrooms, sleeps twelve, and includes a private pool, spa, and barbecue grills, along with free Wi-Fi.
Beautiful 3br Home Near Lake Mi - Sheboygan, WI
9.8 47 reviews

Beautiful 3br Home Near Lake Mi

apartment, Sheboygan
This Sheboygan apartment is a family-friendly option with excellent user, location, and cleanliness ratings. It accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, parking, and internet access.
The apartment is conveniently located in Sheboygan, offering easy access to local attractions and activities. It boasts a comfortable layout with one bathroom and a spacious living area, making it an ideal choice for families or groups seeking a memorable vacation rental.
Beachfront Holiday House On The Lake - Sheboygan, WI
10 5 reviews

Beachfront Holiday House On The Lake

apartment, Sheboygan
This five-bedroom, three-bathroom house in Sheboygan offers stunning views of Lake Michigan from its hilltop location directly across from North Beach and Peace Park, a short walk from downtown.
The fully renovated home features a sunroom, private rooftop deck, and ample outdoor space, comfortably accommodating four guests and providing easy access to Sheboygan's attractions.

Best Sheboygan, WI vacation rentals with a pool

Among the 387 accommodations in Sheboygan, WI, here are the 4 best rentals 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 luxury resort-style apartment overlooks an environmental park with hiking trails and a river in Sheboygan, Wisconsin. It has excellent user, location, and cleanliness ratings.
The apartment has four bedrooms, three bathrooms, and can accommodate up to eight guests. It features a full Viking kitchen, three indoor fireplaces, a lower-level bar, a sunroom, custom bathrooms, and a laundry room. Guests can enjoy amenities such as an indoor lap pool and hot tub, a hand-hewn sauna, a large heated outdoor in-ground pool, multi-level decks with lush furnishings and fire tables, a 2-story heated gazebo with seating and a fire table, an outdoor bar, gas and charcoal grills, and a "band room" that can convert to a fourth bedroom.
Blue Harbor Resort And Conference Center - Sheboygan, WI
8.4 524 reviews

Blue Harbor Resort And Conference Center

resort, Sheboygan
Blue Harbor Resort and Conference Center sits right on the Sheboygan beach, just a short walk from the John Michael Kohler Arts Center, Stefanie H. Weill Center for the Performing Arts, and Above & Beyond Children's Museum. This resort consistently receives very good ratings from previous guests.
The resort offers a variety of accommodations for couples and families. Guests can enjoy a full-service spa, a complimentary waterpark, a fitness center, a restaurant, a bar, and a garden.
Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
10 10 reviews

Luxury Pool Retreat-2 Acres-near Whistling Straits

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 9 reviews

Baronwood Oasis | Pool + Arcade Mega Estate

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
No reviews

The Beach Town Bungalow

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.
Dog-friendly Sheboygan Home - 1 Mi To Town! - Sheboygan, WI
9.7 3 reviews

Dog-friendly Sheboygan Home - 1 Mi To Town!

house, Sheboygan
This pet-friendly vacation home in Sheboygan is located one mile from downtown, offering easy access to shops and restaurants, and less than two miles from South Side Municipal Beach and General King Park Beach.
This 860-square-foot house features one bedroom, one bathroom, and can accommodate three guests, boasting a fully equipped kitchen with a dishwasher, microwave, and refrigerator, plus free Wi-Fi, air conditioning, and a private patio.
Historic Brick Charmer In The Heart Of Sheboygan - Sheboygan, WI
9.7 81 reviews

Historic Brick Charmer In The Heart Of Sheboygan

apartment, Sheboygan
This Sheboygan vacation home is located in the Ellis Historical District, just a 10-minute walk from the John Michael Kohler Arts Center and Lake Michigan. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 3-bedroom home comfortably accommodates up to 6 guests. Enjoy amenities like a swimming pool, a garden, barbecue grills, and a fully equipped kitchen, making it perfect for family vacations or group getaways.
3 Blocks From Beach House 1 Bdrm Full Bath 4 Min To Downtown,sleeps 4 - Sheboygan, WI
9.8 18 reviews

3 Blocks From Beach House 1 Bdrm Full Bath 4 Min To Downtown,sleeps 4

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

Dog-friendly Sheboygan Home - 1 Mi To Town! - Sheboygan, WI
10 26 reviews

Dog-friendly Sheboygan Home - 1 Mi To Town!

apartment, Sheboygan
This Sheboygan vacation rental is located within two kilometers of Lake Michigan, the Blue Harbor Resort & Conference Center Water Park, and Aurora Clinic.
The 860-square-foot house features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, patio, and access to barbecue grills; nearby attractions include St. Peter Claver Parish and the University of Wisconsin-Sheboygan.
Waterfront Sheboygan Condo - Sheboygan, WI
9.6 5 reviews

Waterfront Sheboygan Condo

apartment, Sheboygan
This riverfront condo offers direct access to Sheboygan's boardwalk, located a 5-minute walk from South Shore public beach and within walking distance of local restaurants and shops.
This spacious, open-concept, two-story apartment features 3 bedrooms, 2 bathrooms, and a loft, accommodating up to 12 guests with amenities including a fully equipped kitchen, in-unit laundry, and provided beach essentials.
Black River Retreat - Sheboygan, WI
9.7 45 reviews

Black River Retreat

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.
Lg Executive Home, Kohler Golf, Eaa, Road America - Sheboygan, WI
No reviews

Lg Executive Home, Kohler Golf, Eaa, Road America

apartment, Sheboygan
This spacious 6-bedroom home is located in a wooded area just four miles from Kohler Golf and the American Club, offering a peaceful retreat close to Sheboygan's attractions. This rental comfortably accommodates 14 guests with three bathrooms and a large living area. Enjoy the fully equipped gourmet kitchen, outdoor patio, gas grill, fire pit, and fitness center, as well as WiFi and a wood-burning campfire.
©2026 cozycozy.com