Sheboygan County Vacations & Trips from $499
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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
Sheboygan
Kohler
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.
Super 8 by Wyndham Appleton
$871
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Appleton (ATW)
6.8/10 (1,004 reviews)
The Super 8 in Appleton was nice. The hotel is dated, but was very quiet, appeared to be rather clean. The bed was comfortable. The only negative is that initially when we walked into our room it smelled of old cigarette smoke, but that smell dissipated very quickly and was NOT on our clothing when we left the room. The staff was very friendly. We would definitely stay there again.
Reviewed on Sep 28, 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
Grandstay Residential Suites Hotel - Sheboygan
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
$132 nightly
$150 total
Nov 3 - Nov 4
Total with taxes and fees
Blue Harbor Resort and Conference Center
725 Blue Harbor Drive Sheboygan WI
$207 nightly
$235 total
Oct 5 - Oct 6
Total with taxes and fees
Watershed Hotel
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
$119 nightly
$135 total
Oct 9 - Oct 10
Total with taxes and fees
9.8/10 Exceptional! (672 reviews)
"Nice hotel"
Reviewed on Oct 3, 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.
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.
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.
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.
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.
Wade House Historic Site
You can spend an afternoon browsing the exhibits at Wade House Historic Site during your trip to Glenbeulah. Stroll along this quaint area's lakeside, or simply enjoy its bars.
What to do in Sheboygan County
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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.
