Sheboygan Vacation Packages

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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.

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Sheboygan Hotel Deals

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 CA $126 per night from Aug 5 to Aug 6
CA $126
CA $143 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"We enjoyed our stay very much, food and atmosphere were wonderful, food was good, and our room was very clean. Staff was helpful and friendly and the location was convenient to all we needed."

Reviewed on Jul. 22, 2025

AmericInn by Wyndham 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 CA $111 per night from Aug 11 to Aug 12
CA $111
CA $125 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (55 reviews)
"The staff was very friendly and helpful!"

Reviewed on Jul. 21, 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 CA $227 per night from Jul 27 to Jul 28
CA $227
CA $258 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (355 reviews)
"One of the prettiest views from a room I’ve stayed in. Large room, comfortable bed, beautiful river views with amazing private deck. Will stay again."

Reviewed on Jul. 22, 2025

Watershed Hotel
See all 674 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Sheboygan

Blue Harbor Resort & Conference Center Water Park

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

What to do in Sheboygan

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

CA $138
per adult
Sheboygan Arts & Water Segway Tour w/ Private Tour Option
Sheboygan Showdown Scavenger Hunt

Sheboygan Showdown Scavenger Hunt

CA $37
per adult
Sheboygan Showdown Scavenger Hunt
Private Professional Golf Experience in American Club Wisconsin

Private Professional Golf Experience in American Club Wisconsin

CA $303
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 can pick up a vacation package to this popular destination on Expedia. However, how much your vacation to Sheboygan costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Sheboygan?
You can generally find reduced prices and greater availability in January, February and April. Browse our cheap Sheboygan vacation packages and you could get some great off-season deals.
How many days is enough for Sheboygan?
We'd recommend booking a Sheboygan vacation for at least 2 days. This will allow you time to check off key attractions including Stefanie H. Weill Centre for the Performing Arts and Above & Beyond Children's Museum, as well as check out neighbourhoods like Downtown Sheboygan and Ellis Historical District. You might even be able to make time for one or two day trips beyond Sheboygan.
Is it worth booking a vacation package to Sheboygan?
Sheboygan has all the ingredients you need for an amazing trip — family-friendly attractions, cycling and watersports are just the start. Whether you want to check out sights like Blue Harbour Resort & Conference Centre Water Park and John Michael Kohler Arts Centre, or take the road less travelled, you'll find plenty to see and do on your Sheboygan vacation.
How to find the best Sheboygan package deals?
Finding a cheap Sheboygan package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Sheboygan package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Sheboygan vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can personalize your Sheboygan trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Sheboygan?
If you've got your Sheboygan vacation dates confirmed, book early to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Sheboygan?

  1. Pick your dates: What you'd like to do in Sheboygan and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Sheboygan.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Sheboygan. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Sheboygan vacation package.

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