Sheboygan County vacation rentals

We found 456 vacation rentals — enter your dates for availability

Discover a selection of 223 homes, 63 apartments, and other vacation rentals in Sheboygan County that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, such as air conditioning and a TV. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Popular Sheboygan County destinations on Vrbo

Vacation rentals with weekly discounts - Sheboygan County

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Find out more about Sheboygan County

Why visit Sheboygan County

  1. Outdoor Adventures: Enjoy a variety of activities like hiking, biking, and water sports in the scenic landscapes of Sheboygan County.
  2. Cultural Experiences: Discover local history through museums, historic houses, and art galleries that showcase the region's rich heritage.
  3. Charming Downtown: Stroll through downtown Sheboygan, featuring unique shops, restaurants, and vibrant art scenes.
  4. Family-Friendly Activities: Engage in numerous activities suitable for all ages, making it a great destination for families.
  5. Romantic Getaways: Experience intimate settings perfect for couples, from waterfront dining to cozy accommodations.

Top attractions in Sheboygan County

Sheboygan County, Wisconsin, offers a perfect blend of outdoor adventures and romantic getaways, making it an ideal vacation spot. Visitors can explore a variety of attractions, including historic houses, museums, and art galleries, catering to those seeking cultural experiences, family-friendly activities, and scenic beauty. Whether you're looking to immerse yourself in local history or enjoy the great outdoors, Sheboygan County has something for everyone.

  1. Kohler Design Center: This museum showcases the innovative design and craftsmanship of Kohler products. Visitors can explore interactive exhibits, stunning displays of kitchen and bath designs, and gain insight into the company's rich history and commitment to sustainability.
  2. John Michael Kohler Arts Center: A vibrant art museum featuring contemporary works and unique installations. The center offers engaging programs and exhibits that celebrate creativity and connect visitors with local artists and the community.
  3. Wade House Historic Site: Step back in time at this historic house, which highlights Wisconsin's early settlement era. Explore the beautifully restored buildings, enjoy guided tours, and immerse yourself in the fascinating stories of the past.

Things to do recommended for couples

Ready for a romantic getaway in Sheboygan County? Enjoy a delightful meal at Antoinette, where the ambiance sets the perfect mood. Explore the charming local parks or take a scenic walk along the lakefront for a memorable couple's experience.

Things to do recommended for families

Your family will have a blast at the Blue Harbor Resort & Conference Center Water Park, enjoying thrilling water slides and pools. For a relaxing day, visit Kohler-Andrae State Park or Veteran's Park to unwind amidst nature's beauty. Sheboygan County offers the perfect blend of adventure and tranquility!

What do I need to keep in mind when booking a vacation in Sheboygan County

When planning your trip, whether you're traveling with a group, with family, bringing along pets, or seeking extended stays, be sure to prioritize your preferences using the right filters. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Sheboygan County with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Sheboygan County with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sheboygan County: For many families, a vacation wouldn’t feel complete without their furry companions. If you relate to this, consider exploring Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds to ensure that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Sheboygan County: If you're in search of vacation rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Sheboygan County

Sheboygan County, Wisconsin, offers a delightful blend of outdoor adventure and scenic beauty, perfect for family-friendly and romantic getaways. Explore vibrant downtown Sheboygan, with its charming shops and art scenes, or venture into nearby neighborhoods for a taste of local culture. Whether you’re seeking luxury or budget-friendly options, this picturesque region is sure to provide unforgettable experiences, making it an ideal stop for Milwaukee vacations and beyond.

  • Sheboygan: Nestled along the western shore of Lake Michigan, Sheboygan is a vibrant city known for its stunning waterfront and outdoor adventures. Visitors are drawn to its beautiful beaches, scenic parks, and recreational areas perfect for biking, hiking, and picnicking. Sheboygan is also home to popular attractions like the water park and golf courses, offering fun for the whole family. The city’s charming downtown features a mix of local shops, restaurants, and art galleries, making it ideal for leisurely strolls. Whether you’re looking for romance or outdoor fun, Sheboygan provides a picturesque setting for an unforgettable getaway.
  • Elkhart Lake: Elkhart Lake is a quaint village renowned for its crystal-clear lake and relaxing atmosphere. This charming destination is perfect for those seeking outdoor experiences, with opportunities for boating, swimming, and hiking in the surrounding nature. The village is also famous for its historic racetrack, which attracts motorsport enthusiasts from around the country. Elkhart Lake is a great place for couples, featuring cozy accommodations and beautiful scenery, making it an ideal romantic retreat. Enjoy leisurely walks by the lake, dine at local eateries, or explore the nearby national state park for a mix of relaxation and adventure.
  • Kohler: Known for its upscale amenities and beautiful landscapes, Kohler offers a unique blend of outdoor sports and relaxation. This charming city features world-class golf courses set against the backdrop of lush greenery and serene lakes. Visitors can enjoy recreational activities like hiking and biking in the nearby national state park or unwind at local spas and wellness centers. The local beaches provide a perfect spot for sunbathing and water activities. Kohler is also famous for its art and architecture, with stunning buildings that add to its allure. It’s a top choice for sports enthusiasts and those looking to indulge in a little luxury.

Booking with Vrbo is a breeze

Are you aiming to save money on your upcoming journey? Being flexible with your travel dates can be a great strategy, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash™ on your entire booking. Being the organizer certainly has its perks! By joining our OneKey rewards program, you can unlock exclusive savings for members and earn OneKeyCash™ on eligible stays. Sign up today and begin accumulating your rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform where you can easily create new travel plans, pick up from where you last left off, or view and organize your existing itineraries. You'll find your saved or booked properties neatly arranged under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

Choose a vacation rental for your Sheboygan County getaway

Experience the unique character of Sheboygan County with a stay in a vacation home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Sheboygan County

Do you want to discover things to do in the city? Venture out of your vacation home and experience everything that makes Sheboygan County a fun place to get away. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Blue Harbor Resort & Conference Center Water Park (0.5 mi / 0.8 km)
  • Blackwolf Run (3.4 mi / 5.5 km)
  • The Bull at Pinehurst Farms Golf Course (5.6 mi / 9 km)
  • Whistling Straits Golf Course (7 mi / 11.3 km)
  • Road America (14.1 mi / 22.8 km)
  • Port Washington Ghost Walk (26.2 mi / 42.2 km)

Exploring the natural landscape of Sheboygan County

Whether you're an active traveler or just want to appreciate the scenery, Sheboygan County is a great place to spend some time outside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • North Side Municipal Beach (0.7 mi / 1 km)
  • Bookworm Gardens (2.1 mi / 3.4 km)
  • Kohler Park Dunes State Natural Area (5.9 mi / 9.5 km)
  • North Beach (17.9 mi / 28.7 km)
  • Wilke Lake (19.4 mi / 31.3 km)
  • Kettle Moraine Lake (25.7 mi / 41.3 km)

Frequently asked questions

What is the best area to stay in Sheboygan County when booking a vacation rental?
Plymouth is among the more preferred areas to book a vacation property in Sheboygan County. Looking for some cool things to do here? Be sure to visit Evergreen Golf Course and Sheboygan County Fairgrounds.
What is the most popular type of vacation rental accommodation in Sheboygan County?
Based on our research, condos are the most in-demand vacation rental type in Sheboygan County. But having said that, everyone's idea of an awesome stay differs. Vrbo has vacation rentals in a variety of sizes and shapes, and we'll help you find your ideal match.
How much does it cost to rent a vacation rental in Sheboygan County?
The average price for a vacation rental in Sheboygan County is determined by a number of factors, including length of stay, season and property type. Whether you'd like a sprawling villa with space for the whole family or a cozy cottage perfect for just you and the kids, just enter your travel dates to see stays with fantastic value.
How much does it cost to rent a beach house in Sheboygan County?
The average price for a vacation rental close to the beach in Sheboygan County depends on when you're traveling and the size and type of property you're looking for. You can easily and quickly find prices on Vrbo by entering your destination and travel dates. Then make use of the filter tool to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.
Are there pet-friendly vacation rentals in Sheboygan County?
With 40 properties that welcome four-legged guests, your furry buddy can also come along on your Sheboygan County getaway. Use the filter tool to browse our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
Are there large group vacation rentals in Sheboygan County?
With 81 properties that can sleep 10 or more people in Sheboygan County, there's no need to keep anyone off the invite list. From family vacations to events like birthday parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there one-bedroom vacation rentals in Sheboygan County?
You'll find 21 one-bedroom properties in Sheboygan County to choose from. A one-bedroom vacation rental is a great option if it's just you and your sweetheart or if you're traveling alone. Toss in more convenience, privacy and space than a hotel, and you've got yourself a trip to remember.
Can I find two-bedroom vacation rentals in Sheboygan County?
Gather your besties and enjoy peace, privacy and comfort in one of the 65 two-bedroom vacation properties Sheboygan County has to offer.
Are there vacation rentals with WiFi in Sheboygan County?
Whether you'd like to keep up with world events, send a few emails or surf your social networks, there are 152 vacation homes with WiFi in Sheboygan County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Sheboygan County?
Sheboygan County has 257 vacation rentals where you'll be able to wind down in air-conditioned comfort. To book a stay on Vrbo with this perk, choose your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Sheboygan County?
The minimum required age is generally 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Sheboygan County vacation home before making a booking.
How long can I rent a vacation rental in Sheboygan County for?
How long you can book a vacation rental in Sheboygan County is down to the property. Just enter your desired dates to look at a list of options offering extended stays. With loads of creature comforts such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to discover somewhere just right to call your home away from home in Sheboygan County.
Does Vrbo offer discounts for vacation homes in Sheboygan County?
On Vrbo, we've got plenty of great bargains and discounts for Sheboygan County. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're after a mini getaway or an extended stay, Vrbo offers lots of options for every style and budget.

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