Sheboygan Trips (flight + hotel)

Photo by Gene LeSage

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 P4,315 per night from Sep 7 to Sep 8
P4,315
P4,897 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (64 reviews)
"Nice place to stay"

Reviewed on Aug 11, 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 P9,499 per night from Aug 14 to Aug 15
P9,499
P10,781 total
Aug 14 - Aug 15
includes taxes & fees
9.6/10 Exceptional! (376 reviews)
"Very happy with our stay"

Reviewed on Aug 10, 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 P5,286 per night from Aug 24 to Aug 25
P5,286
P5,999 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"The room was spacious and clean. The breakfast has healthy choices but the area did not have enough seating. Parking was easy."

Reviewed on Aug 10, 2025

AmericInn by Wyndham Sheboygan
See all 671 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

Bookworm Gardens

Explore the great outdoors at Bookworm Gardens, a lovely green space in Sheboygan. Wander the lakeside and beautiful beaches in this family-friendly area.

Bookworm Gardens

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.

Sheboygan South Pier

What to do in Sheboygan

Sheboygan Showdown Scavenger Hunt

Sheboygan Showdown Scavenger Hunt

P1,687
per adult
Sheboygan Showdown Scavenger Hunt
Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

P5,873
per adult
Sheboygan Arts & Water Segway Tour w/ Private Tour Option
Private Professional Golf Experience in American Club Wisconsin

Private Professional Golf Experience in American Club Wisconsin

P12,737
per adult
Private Professional Golf Experience in American Club Wisconsin
See all activities in Sheboygan

Frequently asked questions

How much does a Sheboygan vacation 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 vacation 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 vacation packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and accommodations.
How many days is enough for Sheboygan?
To fully enjoy a Sheboygan vacation, we suggest staying for 2 days. Split your time between visiting Stefanie H. Weill Center for the Performing Arts, Above & Beyond Children's Museum and other key sights, on top of experiencing neighborhoods like Downtown Sheboygan and Ellis Historical District. If you've got some time to spare, include a day trip in your Sheboygan vacation itinerary.
Is it worth booking a vacation 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 Harbor Resort & Conference Center Water Park and John Michael Kohler Arts Center, or take the path less traveled, you'll find plenty to experience 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. Choose your travel dates: What you plan to do in Sheboygan and your favorite season can help you decide when to travel.
  2. Plan your budget wisely: On top of the cost of your accommodations, 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 accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Sheboygan vacation package for you.

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