Sheboygan County Vacation Rentals, Wisconsin: house rentals & more

Discover a selection of 213 homes, 51 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.

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Sheboygan County

Classy? Yes, but comfy, too! Enjoy yesteryear's elegance with modern perks.

Summer’s right around the corner! Book your group vacay while the going’s good.

Sleeps 24 · 10 bedrooms · 6+ bathrooms

The private, beautiful 2 acre lakeside lot is surrounded by forest.

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Sleeps 14 · 4 bedrooms · 3+ bathrooms

Seagull Beach, Lake Michigan Cottage - Open for the NFL Draft 260/night for 2-4

Sleeps 2 · 1 bedroom · 2 bathrooms

Top rated rentals - Sheboygan County

Beautiful sunrise view from our lakeview property! These colors!!!

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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:

Bookworm Gardens (2.1 mi / 3.4 km)
North Beach (17.9 mi / 28.7 km)
South Beach (18.8 mi / 30.2 km)
Wilke Lake (19.4 mi / 31.3 km)
Wolf Lake (25.8 mi / 41.6 km)
North Side Municipal Beach (0.7 mi / 1 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.