Sheboygan County Vacations & Trips from $585
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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
Kohler
Sheboygan
Elkhart Lake
Plymouth
Sheboygan Falls
Oostburg
Cleveland
Cedar Grove
Random Lake
The Latest Sheboygan County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Best Western Plus Paper Valley Hotel
$585
per person
Nov 13 - Nov 16
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Appleton (ATW)
8.4/10 Very Good! (1,011 reviews)
Overall this was a decent hotel. We stayed 3 nights. The A/C in room 216 did not work. The usb ports were all trashed. The light by the bed flickered with a bad short. The shower curtain was too small. The staff graciously moved us to Room 116. Much better! The breakfast offerings were great, and warm! Be aware that the entrance to the motel is very tricky. Almost dangerous due to the busy intersection out front.
Reviewed on Aug 17, 2026
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
838 N 15th St Sheboygan WI
$181 nightly
$206 total
Aug 20 - Aug 21
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
$143 nightly
$162 total
Aug 23 - Aug 24
Total with taxes and fees
8.6/10 Excellent! (1,072 reviews)
"The area was okay, close to the downtown as well as close to the farmers market area. There was never anyone at the front desk, only a button to push when you wanted to get someones attention. Breakfast wasnt anything to write home about. It was an okay stay for the price."
Reviewed on Aug 18, 2026
AmericInn by Wyndham Sheboygan
3664 S Taylor Dr Sheboygan WI
Fully refundableReserve now, pay when you stay
$97 nightly
$110 total
Sep 8 - Sep 9
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"The air conditioner was stuck on “on”. We had to unplug it to stop it from getting too cold. The breakfast was very simple. The room was clean and the hotel was quiet."
Reviewed on Aug 17, 2026
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.
Stay near popular Sheboygan County attractions
Road America
9.4/10 (240 reviews)
You can take time to visit Road America during your travels to Plymouth. Discover the area's waterfalls and coffeehouses.
Whistling Straits Golf Course
9.4/10 (20 reviews)
Enjoy a round of golf in Sheboygan at Whistling Straits Golf Course. Wander the lakeside and beautiful beaches in this family-friendly area.
The Bull at Pinehurst Farms Golf Course
8.0/10 (2 reviews)
Enjoy a round of golf in Sheboygan Falls at The Bull at Pinehurst Farms Golf Course. While you're in the area, stroll along the lakeside.
Blackwolf Run
9.2/10 (39 reviews)
Enjoy a round of golf in Kohler at Blackwolf Run. Wander the lakeside in this family-friendly area.
Sheboygan South Pier
You can find out about the history of Sheboygan with a visit to Sheboygan South Pier. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
John Michael Kohler Arts Center
9.4/10 (81 reviews)
You can spend time browsing the exhibits at John Michael Kohler Arts Center during your travels in Sheboygan. Wander the lakeside in this family-friendly area.
Kohler Design Center
9.4/10 (53 reviews)
You can spend time browsing the exhibits at Kohler Design Center during your trip to Kohler. While you're in the area, stroll along the lakeside.
What to do in Sheboygan County
Sheboygan Segway Tour w/ Private Tour Option
$101
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
