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.
Kinn Guesthouse Bay View
Bay View
Price was CA $980, price is now CA $893 per person
CA $893
per person
May 5 - May 7
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
Scent sensitive people, beware. They use scented detergent on their linens, if you're sensitive to that kind of stuff. The staff was great at fixing my issues, but I took a refund and left after one night. When I arrived, the common area and the room was over 80 degrees. It took hours and several phone calls to work through the issue. I was moved to another room but the heat issue persisted. It wasn't until 3 am that the room finally got to 70 degrees. Also, I carry a white noise machine because hotels can get noisy. But I was still able to hear people banging around in the shared kitchen throughout the entire night. So, after one night of no sleep, I decided to take their offer to refund my second night and let me leave. I just have up on all my plans and went home. But staff and management were dilligent in addressing my issues.
Reviewed on Feb 15, 2026
The Pfister Hotel
Downtown Milwaukee
Price was CA $1,398, price is now CA $1,224 per person
CA $1,224
per person
May 5 - May 7
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
9.6/10 Exceptional! (1,786 reviews)
The location is beautiful. Staff was amazing. The room was comfortable and great
Reviewed on Feb 26, 2026
Fairfield Inn & Suites by Marriott Milwaukee Downtown
Westown
Price was CA $1,287, price is now CA $1,141 per person
CA $1,141
per person
May 5 - May 7
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
8.2/10 Very Good! (1,000 reviews)
Amazing staff and very welcoming! Fresh cookies, amazing breakfast options and clean B rooms!
Reviewed on Feb 27, 2026
Hilton Milwaukee
Westown
Price was CA $1,450, price is now CA $1,287 per person
CA $1,287
per person
May 5 - May 7
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
8.4/10 Very Good! (1,075 reviews)
Everything was lovely. The updates in the lobby are jaw dropping, and the puppies are so cute.
Reviewed on Feb 27, 2026
Hampton Inn & Suites Milwaukee Downtown
Westown
Price was CA $1,186, price is now CA $1,062 per person
CA $1,062
per person
May 5 - May 7
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Milwaukee (MKE)
6.6/10 (1,003 reviews)
Clean room, god breakfast, nice staff. Walking distance to Fiserv and the deer district
Reviewed on Feb 25, 2026
Sheboygan Hotel Deals
Watershed Hotel
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Mar 1 to Mar 2
CA $147
CA $167 total
Mar 1 - Mar 2
includes taxes & fees
9.6/10 Exceptional! (491 reviews)
Wonder welcome, clean and spacious room
Reviewed on Feb 25, 2026
Blue Harbor Resort and Conference Center
725 Blue Harbor Drive Sheboygan WI
The price is CA $251 per night from Mar 1 to Mar 2
CA $251
CA $321 total
Mar 1 - Mar 2
includes taxes & fees
8.4/10 Very Good! (458 reviews)
All was good
Reviewed on Feb 23, 2026
La Quinta Inn by Wyndham Sheboygan
2932 Kohler Memorial Dr Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Mar 15 to Mar 16
CA $105
CA $119 total
Mar 15 - Mar 16
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
good service
Reviewed on Feb 24, 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 $305
per adult
Explore a world of travel with Expedia
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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.
