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.
Top Sheboygan Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Potawatomi Hotel & Casino
Menomonee River Valley
Price was CA $2,098, price is now CA $1,713 per person
CA $1,713
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,469 reviews)
The hotel was clean with outstanding service and the casino was amazing!! Definitely look forward to visiting again!
Reviewed on May 19, 2026
The Pfister Hotel
Downtown Milwaukee
Price was CA $2,782, price is now CA $1,987 per person
CA $1,987
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
9.6/10 Exceptional! (2,101 reviews)
I thoroughly enjoyed the staff they were 5* customer service. The bars and restaurant choices were great too.
Reviewed on May 19, 2026
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was CA $2,335, price is now CA $1,813 per person
CA $1,813
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
9.8/10 Exceptional! (2,653 reviews)
Sadly only staying for one night but the hotel was excellent and I’d recommend. Lots of nice musical touches in the rooms. Would stay again.
Reviewed on May 14, 2026
Kinn Guesthouse Bay View
Bay View
Price was CA $2,656, price is now CA $2,155 per person
CA $2,155
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
9.4/10 Exceptional! (461 reviews)
Love the decor. Felt like home! Walking distance to coffee & dinner places was great!
Reviewed on May 8, 2026
Sheboygan Hotel Deals
Watershed Hotel
838 N 15th St Sheboygan WI
The price is CA $179 per night from May 21 to May 22
CA $179
CA $203 total
May 21 - May 22
includes taxes & fees
9.6/10 Exceptional! (542 reviews)
"The hotel is new, very clean and the staff were terrific! I stayed in a suite, it was spacious, well furnished and had a large balcony. No view, but still a great room."
Reviewed on May 17, 2026
Blue Harbor Resort and Conference Center
725 Blue Harbor Drive Sheboygan WI
The price is CA $253 per night from May 28 to May 29
CA $253
CA $323 total
May 28 - May 29
includes taxes & fees
8.4/10 Very Good! (465 reviews)
"Good views but staff qas not helpful. The bed cover was dirty. Coffee onlynhad one pack of creamer."
Reviewed on May 17, 2026
AmericInn by Wyndham Sheboygan
3664 S Taylor Dr Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Jun 3 to Jun 4
CA $116
CA $131 total
Jun 3 - Jun 4
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"The staff did not cleaned my room at all"
Reviewed on May 19, 2026
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
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.
What to do in Sheboygan
Sheboygan Segway Tour w/ Private Tour Option
CA $138
per adult
Private Professional Golf Experience in American Club Wisconsin
CA $301
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
