Sheboygan County Vacations & Trips from $554

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Your Sheboygan County Vacation

Make planning your next big adventure simple with a Sheboygan County vacation package. Whether it's the cuisine, history or something else entirely that draws you here, our package deals will help you discover it all. With so many things to see and do on a trip to Sheboygan County, it can be difficult to know where to begin. Kick off your travels in Sheboygan at Blue Harbor Resort & Conference Center Water Park and Kohler-Andrae State Park — two leading attractions here. Another city worth adding to your itinerary is Random Lake. Don't miss Ozaukee County Pioneer Village and Luxembourg American Cultural Center. From the instant you book your Sheboygan County vacation to when you get back home, Expedia has your back each step of the way.

Top destinations in Sheboygan County

The Latest Sheboygan County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Paper Valley Hotel
 Random Lake Motel (RLM)
Best Western Premier Bridgewood Resort Hotel
Days Inn by Wyndham Neenah
DoubleTree by Hilton Neenah

Find the Best Sheboygan County Vacation Packages

Sheboygan County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
James Tellen Woodland Sculpture Garden, Old Plank Road Trailhead and Sheboygan County Historical Museum

Sheboygan County Hotel Deals

Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $148 total per night from May 27 to May 28
$148 total
May 27 - May 28
Total with taxes and fees
9.6/10 Exceptional! (547 reviews)
"Room was clean and spacious"

Reviewed on May 23, 2026

Watershed Hotel
The American Club

The American Club

5 out of 5
419 Highland Drive Kohler WI
Fully refundableReserve now, pay when you stay
$521 nightly
The price is $575 total per night from May 26 to May 27
$575 total
May 26 - May 27
Total with taxes and fees
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
$127 nightly
The price is $145 total per night from May 31 to Jun 1
$145 total
May 31 - Jun 1
Total with taxes and fees
8.6/10 Excellent! (1,034 reviews)
"Very clean and quiet! Amazing room amenities! Very pleased with our stay!"

Reviewed on May 24, 2026

Grandstay Residential Suites Hotel - Sheboygan
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.