Sheboygan Holidays

Photo by Gene LeSage

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Top hotels in Sheboygan

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 S$118 per night from 20 Jul to 21 Jul
S$118
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (45 reviews)
"I liked my stay"

Reviewed on 2 Jul, 2025

Comfort Inn & Suites Sheboygan I-43
Watershed Hotel
Watershed Hotel
3 out of 5
838 N 15th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is S$242 per night from 13 Jul to 14 Jul
S$242
13 Jul - 14 Jul
includes taxes & 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 2 Jul, 2025

Watershed Hotel
Quality Inn
Quality Inn
2.5 out of 5
4332 N 40th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is S$116 per night from 20 Jul to 21 Jul
S$116
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (626 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 29 Jun, 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.

Popular places to visit

James Tellen Woodland Sculpture Garden

You can spend time exploring the galleries in James Tellen Woodland Sculpture Garden in Sheboygan. Wander the lakeside in this family-friendly area.

James Tellen Woodland Sculpture Garden

What to do in Sheboygan

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

S$129
per adult
Sheboygan Arts & Water Segway Tour w/ Private Tour Option
Sheboygan Showdown Scavenger Hunt

Sheboygan Showdown Scavenger Hunt

S$28
per adult
Sheboygan Showdown Scavenger Hunt
Private Professional Golf Experience in American Club Wisconsin

Private Professional Golf Experience in American Club Wisconsin

S$282
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.