Sheboygan Vacations

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Find the Best Sheboygan Vacation Packages

Sheboygan Hotel Deals

Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is AED 569 per night from Jul 5 to Jul 6
AED 569
AED 646 total
5 Jul - 6 Jul
includes taxes & fees
9.6/10 Exceptional! (580 reviews)
"The staff was very friendly and the entire hotel was very clean and nicely decorated."

Reviewed on 29 June 2026

Watershed Hotel
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

3 out of 5
3664 S Taylor Dr Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is AED 377 per night from Jul 12 to Jul 13
AED 377
AED 428 total
12 Jul - 13 Jul
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Room was clean however the air conditioner was horribly loud like there was something wrong with it. We had to ask for toilet paper. Pillow smelled weird."

Reviewed on 22 June 2026

AmericInn by Wyndham Sheboygan
Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is AED 708 per night from Jul 5 to Jul 6
AED 708
AED 803 total
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (1,047 reviews)
"Photos of the pool and fitness area are deceiving. Those two areas are tiny. Everything else was good."

Reviewed on 1 July 2026

Grandstay Residential Suites Hotel - Sheboygan
See all 707 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.

Stay near popular Sheboygan attractions

Blue Harbor Resort & Conference Center Water Park

8.6/10 (143 reviews)
This lakeside resort boasts a 54,000-square-foot indoor water park with thrilling slides and a surf simulator. Enjoy year-round aquatic fun while taking in picturesque views of Lake Michigan from your room.
See properties

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 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.