Wisconsin may have travel restrictions in place due to COVID-19.

Travel to Sheboygan

Choose two or more items and save on your trip:

Sheboygan Vacation: Coronavirus Information

Most Sheboygan hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Sheboygan trip, please visit our Coronavirus Information page (opens in new window).

Top Sheboygan Flight + Hotel Deals

Saint Kate The Arts Hotel

2021 Sheboygan vacation deals

Residence Inn Milwaukee Downtown by Marriott
Four Points by Sheraton Milwaukee North Shore
Four Points by Sheraton Milwaukee Airport
DoubleTree by Hilton Milwaukee Downtown
Fairfield Inn & Suites by Marriott Milwaukee Airport

Top Hotels in Sheboygan

Super 8 by Wyndham Sheboygan WI
Super 8 by Wyndham Sheboygan WI
2 out of 5
3402 Wilgus Avenue, Sheboygan, WI
Free CancellationReserve now, pay when you stay
The price is $55 per night from Dec 2 to Dec 3
3.4/5Good! (475 reviews)

"Nice location with short drive to downtown and easy access to highways. Friendly staff and did a nice job cleaning everyday."…"

Reviewed on Oct 12, 2020

Super 8 by Wyndham Sheboygan WI
Blue Harbor Resort and Spa
Blue Harbor Resort and Spa
3 out of 5
725 Blue Harbor Drive, Sheboygan, WI
The price is $151 per night from Dec 2 to Dec 3
4.2/5Excellent! (321 reviews)

"Great location with a view on Michigan lake. Activities for kids were top notch: surfing at water park, glow in dark mini golf, nice arcade and of course the boat house or aquarium rooms.staff at the waterpark was friendly, professional, alert and very welcoming. Great place for family stay."…"

Reviewed on Oct 20, 2020

Blue Harbor Resort and Spa
The American Club
The American Club
5 out of 5
419 Highland Drive, Kohler, WI
Free CancellationReserve now, pay when you stay
The price is $189 per night from Dec 2 to Dec 3
4.7/5Exceptional! (102 reviews)

"I returned to the American Club for a short stay. I just love this property and their staff. Look forward to visiting them again."…"

Reviewed on Nov 29, 2020

The American Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top things to do in Sheboygan

What are the advantages of a road trip to Sheboygan?

There’s nothing quite like a Sheboygan road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Sheboygan or bundle your hotels with car rentals to save even more. With our Sheboygan packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.  

How to plan a road trip to Sheboygan?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Sheboygan and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.  

What to do on a road trip to Sheboygan?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Sheboygan. You can book all the road trip activities on your Sheboygan wishlist, and even plan activities along your route as well.  

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Sheboygan. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

How much does a Sheboygan vacation package cost?
From just $413. Yes, you read that right. Our Sheboygan packages are a simple way to stretch your budget. Bundle your flights, hotels and rental car and get out and see this wonderful destination.
If I'm not able to travel, can I cancel my Sheboygan vacation package?
You can change or cancel your booking, but whether or not you’ll incur a charge will depend on a few things. If you’ve booked a Sheboygan vacation package in the last 24 hours, it may be possible to cancel or change your itinerary for free. For later changes, your hotel, airline or car rental company may impose a charge. Take a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Sheboygan?
Bundle your hotel and flight bookings, add extras such as activities or a rental car, and save up to $583. A Sheboygan vacation package makes getting away easy and cheap for everyone. You won’t just land wonderful discounts on your trip — you’ll have lots of choice at your fingertips too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 hotels all over the world. Your next epic adventure begins right here, right now!
What are the top hotels in Sheboygan?
If you intend to stay in the Manitowoc neighborhood, some top options are Baymont by Wyndham Manitowoc Lakefront and AmericInn by Wyndham Manitowoc. Plymouth is also a popular Sheboygan area. We recommend Baymont by Wyndham Plymouth or AmericInn by Wyndham Plymouth if you prefer this part of the city.
When is the best time of year to visit Sheboygan?
The perfect time to visit Sheboygan depends on you. If you’re vacationing on a limited budget, perhaps avoid , which is considered to be the most expensive time of year. is usually when you’ll pick up the best prices. To enjoy the atmosphere of peak season, pack your bags for . are the least popular months to visit and a good idea if you’d rather escape the crowds.
How far in advance should I book my Sheboygan vacation?
While not all air carriers release ticket prices early, you can usually look up international flights on Expedia up to a year in advance. This is when you can bag some fantastic deals. If you’re booking last minute, you might get lucky. Low prices sometimes become available only weeks before departure.
What does an Expedia Sheboygan travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to create your perfect Sheboygan travel package. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Don’t forget — the more you bundle, the more dollars you’ll save!
What should I know before booking a Sheboygan travel package?
We already have low prices. However, you’ll enjoy even better deals if you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and tons of choice.
Does Expedia offer Book Now, Pay Later Sheboygan vacation packages?
Working together with online lender Affirm, Expedia offers financial freedom with a Book Now, Pay Later option for hotel and flight packages. Get the money side of things sorted with an upfront payment or split the cost of your journey over multiple installments. The choice is yours.
Can I choose my airline with a Sheboygan Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you’re eager to fly to Sheboygan in business or coach, simply choose from the available airline options. Expedia has access to over 550 airline partners across the world.

More trip options