Sheboygan Vacations from $385

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Your Sheboygan Vacation

With a Sheboygan vacation package, discovering the best of this coastal city is simple. From its lively atmosphere and rich history to its family-friendly attractions, this destination has something for everyone to enjoy. Every trip to Sheboygan needs a well-designed itinerary. Fill yours with famous sights like Blue Harbor Resort & Conference Center Water Park, Kohler Design Center and John Michael Kohler Arts Center. Whoever you're heading away with and whatever the size of your budget, your dream Sheboygan vacation is just a few clicks away with Expedia.

The Latest Sheboygan vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
per person
Sep 11 - Sep 15
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
8.4/10 Very Good! (1,000 reviews)
Our room was clean and the bed was very comfortable. Everyone was very helpful and always smiling.

Reviewed on Jul 5, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Save 100% on your flight
per person
Sep 11 - Sep 15
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,006 reviews)
Fantastic! Beautiful property, very quiet and unique. Loved our stay.

Reviewed on Jul 4, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
per person
Sep 11 - Sep 15
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
9.6/10 Exceptional! (388 reviews)
Quiet, walkable, close to everything

Reviewed on Jun 27, 2025

Chalet Motel Mequon

Chalet Motel Mequon

2.5 out of 5
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
8.8/10 Excellent! (1,007 reviews)
We always enjoy staying here when we visit the cedarburg area.

Reviewed on Jul 5, 2025

Hilton Garden Inn Milwaukee Airport

Hilton Garden Inn Milwaukee Airport

3 out of 5
per person
Sep 11 - Sep 15
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,002 reviews)
Great staff, room and convenient to the airport

Reviewed on Jun 29, 2025

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Discover the most popular places to visit in Sheboygan

Blue Harbor Resort & Conference Center Water Park

4/5(30 reviews)

Enjoy a fun-filled day at Blue Harbor Resort & Conference Center Water Park during your trip to Sheboygan. Wander the lakeside in this family-friendly area.

Blue Harbor Resort & Conference Center Water Park

Whistling Straits Golf Course

Enjoy a round of golf in Sheboygan at Whistling Straits Golf Course. Wander the lakeside and beautiful beaches in this family-friendly area.

Whistling Straits Golf Course

John Michael Kohler Arts Center

4.5/5(22 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.

John Michael Kohler Arts Center

What to do in Sheboygan

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

$101
per adult
Sheboygan Arts & Water Segway Tour w/ Private Tour Option
See all activities in Sheboygan

Sheboygan Hotel Deals

Watershed Hotel
Watershed Hotel
3 out of 5
838 N 15th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $210 total per night from Jul 10 to Jul 11
$210 total
Jul 10 - Jul 11
Total includes taxes and fees
9.6/10 Exceptional! (348 reviews)
"Great views from the Riverview room. Nice staff. Lots of room in the hotel and outside on the grounds to hang out. Would stay again."

Reviewed on Jul 2, 2025

Watershed Hotel
Comfort Inn & Suites Sheboygan I-43
Comfort Inn & Suites Sheboygan I-43
2.5 out of 5
3912 Motel Rd, Sheboygan, WI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $92 total per night from Jul 13 to Jul 14
$92 total
Jul 13 - Jul 14
Total includes taxes and fees
8.4/10 Very Good! (41 reviews)
"I liked my stay"

Reviewed on Jul 2, 2025

Comfort Inn & Suites Sheboygan I-43
Quality Inn
Quality Inn
2.5 out of 5
4332 N 40th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Jul 13 to Jul 14
$91 total
Jul 13 - Jul 14
Total includes taxes and fees
8/10 Very Good! (625 reviews)
"Updated room, very clean, brand-new looking, easy parking. Perfect location for RoadAmerca races at an excellent price. Convenient to Sheboygan downtown."

Reviewed on Jun 29, 2025

Quality Inn
See all 669 properties in 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.

Find the Best Sheboygan Vacation Packages

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Frequently asked questions

How much does a Sheboygan vacation package cost?
You'll find cheap prices from $385 on Expedia for your Sheboygan break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Sheboygan costs.
What are the cheapest months to go to Sheboygan?
If you're hoping to score a cheap Sheboygan vacation package, consider planning a trip in December, January and February. You're likely to find lower prices on flights and accommodations during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Sheboygan?
Sheboygan vacations come in many shapes and sizes, but to really sink your teeth into this place, we'd say 2 days is about right. In this timeframe, you can fit in major attractions like Stefanie H. Weill Center for the Performing Arts and Sheboygan County Historical Museum and seek out some lesser-known gems. Don't forget to visit neighborhoods such as Downtown Sheboygan and Ellis Historical District either. If you plan wisely, you can even allow for a day trip or two from Sheboygan too.
Is it worth booking a vacation package to Sheboygan?
Sheboygan has all the ingredients you need for the perfect getaway --- family-friendly attractions, cycling and watersports are just the start. Whether you'd like to visit attractions like Blue Harbor Resort & Conference Center Water Park and John Michael Kohler Arts Center, or venture off the beaten track, you'll find plenty to do on your Sheboygan vacation.
How to find the best Sheboygan package deals?
Use Expedia's handy filters to find some unbeatable Sheboygan package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Sheboygan package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Sheboygan vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights individually. Better still, you can tailor your Sheboygan trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Sheboygan?
If you have your Sheboygan travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Sheboygan?

  1. Pick your travel dates: What you plan to do in Sheboygan and your favorite season can help you decide when to get away.
  2. Plan your budget wisely: In addition to the cost of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may arise during your trip to Sheboygan.
  3. Discover Sheboygan using our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Sheboygan. You can also save your favorite places, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go away for: Now that you're up to speed on Sheboygan, you can work out the ideal length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Sheboygan vacation package for you.
  6. Add on experiences and excursions: Read our travel guide to find some awesome things to do in Sheboygan. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Sheboygan vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Sheboygan vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.