Sheboygan County Vacations & Trips

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Top destinations in Sheboygan County

A warm December day took me here for a walk on Lake Michigan in Wisconsin. Wonderful place, I hope it doesn't turn into a golf course. Great campground here too
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Sheboygan County Hotel Deals

The American Club

The American Club

5 out of 5
419 Highland Drive Kohler WI
Fully refundableReserve now, pay when you stay
The price is ￥68,157 per night from Nov 18 to Nov 19
￥68,157
￥75,314 total
Nov 18 - Nov 19
includes taxes & fees
9.6/10 Exceptional! (232 reviews)
The shower was amazing

Reviewed on Nov 7, 2025

The American Club
Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is ￥18,721 per night from Nov 18 to Nov 19
￥18,721
￥21,247 total
Nov 18 - Nov 19
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Nice and convenient. Right in downtown so very convenient to surrounding areas.

Reviewed on Nov 14, 2025

Grandstay Residential Suites Hotel - Sheboygan
Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is ￥16,190 per night from Nov 18 to Nov 19
￥16,190
￥18,375 total
Nov 18 - Nov 19
includes taxes & fees
9.6/10 Exceptional! (450 reviews)
We stayed here for a little mini-vacation before our baby joins our family. We stayed on the first floor with a river view, and it had direct access to a cute little bench and grass area outside our room. This was GREAT as our pups joined us (for a small, but very fair additional cost). The room ...

Reviewed on Nov 17, 2025

Watershed Hotel
See all 430 properties in Sheboygan County
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.

Frequently asked questions

How much does a Sheboygan County vacation package cost?
Get ready to book, because a trip to Sheboygan County starts from a tempting . When you bundle your flights, hotels and car rentals into a travel package, you'll pick up the biggest bargains.
How do I get a cheap travel package to Sheboygan County?
Bundle your flights and hotels, throw in extras such as activities, and save with a Sheboygan County vacation package. You won't just pick up wonderful discounts on your trip — you'll have a world of choice within your reach too. When you book through Expedia, you can choose from more than 550 partner airlines and 1,000,000 properties across the globe. Your next grand adventure starts right here, right now!
What are the top hotels in Sheboygan County?
For hotels in Sheboygan with friendly service and cozy beds, check out La Quinta Inn by Wyndham Sheboygan and Grandstay Residential Suites Hotel. If you're stopping by Plymouth as well, you'll get a wonderful night's sleep at AmericInn by Wyndham Sheboygan or AmeriVu Inn & Suites.
How far in advance should I book my Sheboygan County vacation?
To bag discount prices, book nice and early. Airlines usually release flight tickets, along with some of the lowest fares, around a year ahead of time. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you've decided on a last-minute getaway in Sheboygan County, there are always lots of great deals to be had on Expedia. Check them out now!
What does an Expedia Sheboygan County travel package include?
Expedia has all you need to lock in Sheboygan County escape, but what goes into your package depends on you. Select from a combination of flights, hotels and rental cars. Chasing a few activities to fill in your time? Once you've made your booking, you can add them too. Whatever your style, there's a deal to suit your needs.
Can I choose my airline with a Sheboygan County Expedia vacation package?
Yes, and with over 550 airlines to choose from all over the world, you're spoiled for choice. Look through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Sheboygan County vacation package?
We totally understand — the universe can throw the odd curveball. If you've booked a Sheboygan County vacation package and have to cancel or amend it, we can help. It's always worth visiting our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.