Discover a selection of 41 vacation rentals in Sheboygan County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $170 per night, and houses and cabins are popular options for a stay in Sheboygan County. Either way, you'll find a rental for everyone's needs.
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Destination guide

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.

Things to do

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)
Natural features

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:

  • Kohler-Andrae State Park (6.7 mi / 10.8 km)
  • Harrington Beach State Park (18 mi / 29 km)
  • Kettle Moraine State Forest (22.4 mi / 36 km)
  • Wilke Lake (19.4 mi / 31.3 km)
  • North Side Municipal Beach (0.7 mi / 1 km)
  • Old Plank Road Trail Head (2.3 mi / 3.7 km)

What are the top vacation rentals in Sheboygan County?

Deluxe villas, tranquil houseboats and quaint cottages — everyone's dream escape is different. Whatever your tastes, you're sure to find something that catches your eye among these top vacation rentals in Sheboygan County:

  • "Seagull Beach Guest House, Lake Michigan Cottage On Private Beach": This Positano retreat offers 1 bedroom and is highly rated among guests. Conveniences such as water sports equipment and a beach help make your stay comfortable.
  • "Newly Remodeled 2 Bed/2bath Townhouse": Stay a week or so at this option in Mont-Saint-Jean and take advantage of a highchair, nearby birdwatching activities and more. It has 2 bedrooms to accommodate your friends and family.

For even more great options, use the search bar at the top of the page to find the perfect Sheboygan County vacation rental for you.

Can I find log cabins to rent in Sheboygan County?

Yes, you can! From rustic retreats to high-end escapes, Vrbo has a range of log cabins to rent in or around Sheboygan County. If you're chasing adventure, here's where you can go:

  • "Valders Log Cabin Near Eea Air Show And Sheboygan": This is a perfect base to try some of the exciting outdoor activities this region has to offer, including hiking and biking and cycling.
  • "Log Cabin On Great Fishing And Boating Lake": Stay in and enjoy the quiet atmosphere or have a go at some of the exciting activities nearby, such as fishing and water skiing. You can be as active or chill as you like.

What are the top-rated vacation rentals for weekend getaways in Sheboygan County?

Whether you're planning a trip with the family, a rendezvous for two or a couple of nights away alone, we have weekend getaways in Sheboygan County to suit your needs. Pack your overnight bag and stay at one of these popular escapes:

  • "Lake Michigan Sand Beach And Wooded Privacy" - Situated in Oostburg, this rental property offers handy extras including a fridge and a nearby laundromat.
  • "Remodeled Home On Lake Michigan" - With an oven and a restaurant dining guide, not to mention its great location in Central Wisconsin, you won't want to check out of this rental.

Can I find studio apartments for rent in Sheboygan County?

If you're chasing something with more personality than a standard hotel room, you'll love our studio apartments in Sheboygan County. Whip up a snack in your kitchenette, scroll through social media on the lounge and feel completely at home. Take a peek at some of our comfiest studios:

  • Settle in and make yourself comfortable at "Seagull Beach Guest House, Lake Michigan Cottage On Private Beach", situated in Positano. There are plenty of amenities at your disposal here, including a garden and a restaurant dining guide.
  • Otherwise, use "Private, Peaceful Retreat Near Road America" as a base to get out and explore the area. This home away from home is in Plymouth and comes with a nearby river and internet services.

Can I find short term rentals in Sheboygan County?

With Vrbo's terrific selection of short-term rentals in Sheboygan County, you're bound to find a place to suit your needs. Whether you're chasing somewhere to chill on your own or to reconnect with friends and family, these options are difficult to beat:

  • Located close to the middle of Oostburg, "Lake Michigan Sand Beach And Wooded Privacy" is well suited to a short-term stay. Set up camp here and visit all the fascinating attractions around the area.
  • Otherwise, bunk down for a few days at "Remodeled Home On Lake Michigan" and discover the best of Central Wisconsin. This property also welcomes short-term guests and is a good choice if you like to be near the action.

What are the best romantic weekend getaways in Sheboygan County?

A romantic weekend getaway in Sheboygan County is a surefire way to rekindle the passion. Light some pretty candles, take your honey by the hand and get set to send sparks flying at one of these vacation rentals:

  • Catch up on quality time and plenty of cuddles at "Seagull Beach Guest House, Lake Michigan Cottage On Private Beach" in Positano. A fireplace and a swimming pool are some of the nice touches on offer here.
  • Alternatively, plan a weekend of canoodling at "Newly Remodeled 2 Bed/2bath Townhouse". A fireplace and a swimming pool add to the idyllic atmosphere of this Mont-Saint-Jean property.

What are the best large group vacation rentals in Sheboygan County?

If your idea of a dream trip away is to bring along all your besties, you'll be needing a whole bunch of space. Luckily, there are many vacation rentals in Sheboygan County that are designed for large groups, starting with these sprawling sensations:

  • "Large Unique And Artistic Lake Michigan Beach House": With 4 bedrooms, everyone can be a part of the fun at this sought-after escape in Oostburg. A water park and a fireplace are among the many amenities available here.
  • "New Game Room, Theater, Large Group": Located in Zagore, this knockout has 5 bedrooms and is another favorite for a large family vacation. There's a whole lot to keep guests both comfortable and entertained, including a garden and a kitchen.

What are the best houses for rent with a pool in Sheboygan County?

Take your pick and hop right in. Here are a couple of top-notch house rentals in Sheboygan County where life is better by the pool:

  • Book a stay at "Large Unique And Artistic Lake Michigan Beach House", where the first item on your itinerary should be dipping a toe in the pool. This retreat is located in Oostburg and features a range of family-friendly amenities, including a separate dining area and a pool table.
  • "Country Guest House - Real Cozy Warm Fire" in Plymouth is another top pick. There's plenty to like about this place apart from its pool, such as a fridge and a microwave oven.

What are the best large family vacation rentals in Sheboygan County?

Vrbo makes it a cinch to track down an amazing family getaway. With quality amenities and ample room for everyone to spread out, these large family vacation rentals in Sheboygan County are a few of our favorites:

  • Located in Lake Michigan, "Remodeled Home On Lake Michigan" has 3 bedrooms and can fit up to 7 guests. Useful amenities here include childrens activities and a living room.
  • Alternatively, make "Large Unique And Artistic Lake Michigan Beach House" your base for a beautiful vacation. Located in Oostburg, this escape has 4 bedrooms that accommodate up to 15 people. A microwave oven and a fridge will help keep everybody happy and comfortable.

If you're eager to visit some family-friendly attractions in Sheboygan County, Blue Harbor Resort & Conference Center Water Park is a standout.

Can I find family cabin rentals in Sheboygan County?

Toast marshmallows and bust out the playing cards. These cabin rentals in Sheboygan County are fantastic bases to relax and unwind with the fam:

  • "Arcadian Cabin At Bishop Branch" - Escape your daily routine at this Viroqua retreat which offers a garden and childrens activities.
  • "Private Cozy Year Round Cabin On Little Spider Lake" – This option in Arbor Vitae is also a big hit with families. Conveniences here include a stereo and a nearby laundromat.

For more options, use the search bar at the top of the page and adjust the filters to find the Sheboygan County vacation rental that's perfect for your needs.

Explore destinations around Sheboygan County

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