Sheboygan Holidays

Book a Hotel + Flight or Car together to unlock savings

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Sheboygan Holiday

Our pick of the best Sheboygan Hotel Deals

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
The price is NZ$155 per night from 1 Sept to 2 Sept
NZ$155
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (58 reviews)
"The staff was very friendly and helpful!"

Reviewed on 21 Jul. 2025

Comfort Inn & Suites Sheboygan I-43
Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St, Sheboygan, WI
The price is NZ$319 per night from 10 Aug to 11 Aug
NZ$319
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (366 reviews)
Spacious
"The room was wonderful and had a door out to the lawn with a nice view of the river My only complaint is that we could hear the person above us walking, which wouldn’t have been such a big deal except for they did a lot of walking back and forth at all hours of the day and night. Still the accommodations ..."

Reviewed on 31 Jul. 2025

Watershed Hotel
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

2 out of 5
3664 S Taylor Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$178 per night from 11 Aug to 12 Aug
NZ$178
11 Aug - 12 Aug
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Close to Highway,Comfortable bed,Staff was polite and helpful."

Reviewed on 30 Jul. 2025

AmericInn by Wyndham Sheboygan
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.

Discover the most popular places to visit in Sheboygan

Blue Harbor Resort & Conference Center Water Park

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

Blue Harbor Resort & Conference Center Water Park

What to do in Sheboygan

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

NZ$168
per adult
Sheboygan Arts & Water Segway Tour w/ Private Tour Option
Sheboygan Showdown Scavenger Hunt

Sheboygan Showdown Scavenger Hunt

NZ$48
per adult
Sheboygan Showdown Scavenger Hunt
Private Professional Golf Experience in American Club Wisconsin

Private Professional Golf Experience in American Club Wisconsin

NZ$369
per adult
Private Professional Golf Experience in American Club Wisconsin
See all activities in Sheboygan

Frequently asked questions

How much does a Sheboygan holiday package cost?
You'll find cheap prices 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 holiday to Sheboygan costs.
What are the cheapest months to go to Sheboygan?
January, February and April are the best times to look for cheap Sheboygan holiday packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and accommodation.
How many days is enough for Sheboygan?
To fully enjoy a Sheboygan holiday, we suggest staying for 2 days. Split your time between visiting Stefanie H. Weill Centre for the Performing Arts, Above & Beyond Children's Museum and other key sights, on top of experiencing neighbourhoods like Downtown Sheboygan and Ellis Historical District. If you've got some time to spare, include a day trip in your Sheboygan holiday itinerary.
Is it worth booking a holiday package to Sheboygan?
Sheboygan has all the ingredients you need for an awesome getaway — family-friendly attractions, cycling and watersports are just the start. Whether you'd like to check out attractions like Blue Harbour Resort & Conference Centre Water Park and John Michael Kohler Arts Centre, or take the path less traveled, you'll find plenty to experience on your Sheboygan holiday.
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 holiday package as soon as possible.
Is it cheaper to book a Sheboygan holiday as a package?
An Expedia holiday 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 holiday 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. Choose your travel dates: What you plan to do in Sheboygan and your favourite season can help you decide when to travel.
  2. Plan your budget wisely: On top of the cost of your accommodation, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Sheboygan.
  3. Determine how many days away: Start by compiling a list of the activities and sights you'd like to experience in Sheboygan. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your accommodation and airfare: Once you've nailed down your travel dates and duration, book the right Sheboygan holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.