Sheboygan County Vacations & Trips from $489
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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.
Comfort Inn Fond Du Lac
$489
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Appleton (ATW)
8.2/10 Very Good! (655 reviews)
Was used for work related stay, enjoyed the quiet, the hot tub for relaxing after long day of wk as it remains open till 11:00pm, will utilize this facility again
Reviewed on Oct 8, 2026
Hotel Retlaw, Trademark Collection by Wyndham
$607
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Appleton (ATW)
9.4/10 Exceptional! (1,005 reviews)
This beautifully remodeled hotel in the middle of downtown was immaculate. The front desk staff was extremely polite, helpful, and generous with their time, offering good advice and directions for navigating the parking structure and the hotel. My room was of generous size with a unique use of the spacing offered by an old, retrofitted downtown building. I would definitely stay at this hotel again!
Reviewed on Oct 5, 2026
Cobblestone Suites Oshkosh
$691
per person
Dec 26 - Dec 30
found 18 hours ago
Roundtrip flight included
Phoenix (PHX) to Appleton (ATW)
8.6/10 Excellent! (999 reviews)
I stayed here and would say you get what you pay for. #1 for me is cleanliness and the room was very clean. The breakfast was where it fell short. There was no protein or anything hot except if you make a waffle. I toasted a bagel but no cream cheese. I stay at lots of places with free breakfast and this one was just a fail. The staff was great. It was also basically empty so it felt a bit weird. I think maybe 5 rooms were full. However, for a total of $100, it was good!
Reviewed on Oct 7, 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
$130 nightly
$148 total
Nov 3 - Nov 4
Total with taxes and fees
8.6/10 Excellent! (1,105 reviews)
"😊"
Reviewed on Oct 7, 2026
Blue Harbor Resort and Conference Center
725 Blue Harbor Drive Sheboygan WI
$207 nightly
$235 total
Oct 11 - Oct 12
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 16 - Oct 17
Total with taxes and fees
9.8/10 Exceptional! (682 reviews)
"Great location to all of Sheyboygan's activities. Staff very friendly and helpful. Large room with a walk-in shower. Comfortable beds. Quiet"
Reviewed on Oct 8, 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.
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.
Elkhart Lake
Commune with nature and explore the great outdoors at Elkhart Lake during your travels in Elkhart Lake. While you're in the area, stroll along the lakeside.
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.
