Sheboygan County Vacations & Trips from $528
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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 Premier Bridgewood Resort Hotel
$561
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Appleton (ATW)
9.4/10 Exceptional! (850 reviews)
We had a wonderful stay at the Best Western Premier Bridgewood Resort Hotel in Neenah, Wisconsin! The hotel was clean, comfortable, and welcoming, and the staff was friendly and helpful. It was a great place to stay, and we truly enjoyed our time there. We would definitely stay again and highly recommend it to anyone visiting the area!
Reviewed on Aug 23, 2026
Hampton Inn Appleton-Fox River Mall Area
$639
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Appleton (ATW)
9.4/10 Exceptional! (1,003 reviews)
Our flight from Denver was delayed 4 times, yet staff at the hotel kept track of it, and made sure we had transportation to the hotel at 1 a.m.
Reviewed on Aug 24, 2026
Cobblestone Inn & Suites-Fremont
$538
per person
Nov 6 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Appleton (ATW)
9/10 Wonderful! (432 reviews)
Very clean property.
Nice hot breakfast.
My only concern was a slow drain in the bathtub.
I will definitely return.
Reviewed on Aug 19, 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
Fully refundableReserve now, pay when you stay
$158 nightly
$179 total
Aug 25 - Aug 26
Total with taxes and fees
9.6/10 Exceptional! (630 reviews)
"The room was clean and comfortable. The breakfast was good"
Reviewed on Aug 23, 2026
Grandstay Residential Suites Hotel - Sheboygan
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
$140 nightly
$159 total
Sep 6 - Sep 7
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 7 - Sep 8
Total with taxes and fees
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.
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.
Sheboygan County Fairgrounds
8.8/10 (15 reviews)
Enjoy an outing to Sheboygan County Fairgrounds during your stay in Plymouth. Discover the area's waterfalls and seek out the golf courses.
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.
