Downtown Sheboygan Vacation Packages

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Top Holiday Package Deals in Downtown Sheboygan

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Sturtevant/Racine

Super 8 by Wyndham Sturtevant/Racine

2 out of 5
per person
Sep 12 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
7.8/10 Good! (578 reviews)
Nice pool and hot tub

Reviewed on May 29, 2025

DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
per person
Sep 12 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.4/10 Very Good! (1,000 reviews)
Older property, friendly staff

Reviewed on Jul. 14, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
per person
Sep 12 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.4/10 Exceptional! (1,006 reviews)
I liked the decor and the theme of the property. I wish the two lights over the bed would have worked.

Reviewed on Jul. 19, 2025

Hyatt Place Milwaukee/Downtown

Hyatt Place Milwaukee/Downtown

3 out of 5
Westown
per person
Sep 12 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,003 reviews)
Nice area. Lots of choices of eating places. Clean and new looking. Comfortable bed and room darkening shades. Found traffic noisy. Bathroom should have a night light but the whole room lit up when I got up at night. Good breakfast that I enjoyed.

Reviewed on Jul. 10, 2025

Hilton Garden Inn Milwaukee Airport

Hilton Garden Inn Milwaukee Airport

3 out of 5
per person
Sep 12 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,000 reviews)
Great staff, room and convenient to the airport

Reviewed on Jun. 29, 2025

Downtown Sheboygan Hotel Deals

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue, Sheboygan, WI
The price is CA $187 per night from Aug 4 to Aug 5
CA $187
CA $212 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (946 reviews)
Happy stay
"Nice room the fitness room is three atomic machines no weights very small just like the pool. The breakfast ok very rudimentary."

Reviewed on Jul. 15, 2025

Grandstay Residential Suites Hotel - Sheboygan
Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan

2 out of 5
723 Center Avenue, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Aug 11 to Aug 12
CA $100
CA $114 total
Aug 11 - Aug 12
includes taxes & fees
6.8/10 (88 reviews)
Sheboygan
"It was a nice stay except for the homeless people hanging around the building and some of them coming inside and taking food when the staff were busy."

Reviewed on Jul. 7, 2025

Wingate 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 10 to Aug 11
CA $111
CA $126 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (54 reviews)
"Had a nice stay here! The highlight was definitely the really big pool — surprisingly large for a hotel, and a great spot to relax. Breakfast was okay; there were enough options to fill up, though the seating area felt a bit confusing and crowded at times. Overall, the hotel was clean and comfortable, ..."

Reviewed on Jul. 12, 2025

Comfort Inn & Suites Sheboygan I-43
See all 458 properties in Downtown 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

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Frequently asked questions

How much does a Downtown Sheboygan vacation package cost?
Starting from as little as CA $901, you can customize your Downtown Sheboygan package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Downtown Sheboygan?
Booking a flight and hotel together with Expedia won't just save valuable time — it'll save you a tidy sum too. A Downtown Sheboygan vacation package makes it a breeze to create your dream adventure. With more than 550 airlines around the world to select from, finding flights that fit your busy schedule won't be hard. In addition to that, we've got over 1,000,000 properties globally to choose from. Now that's what we call choice. No matter who you are, Expedia brings the world within your reach.
Where should I stay in Downtown Sheboygan?
With fascinating attractions such as Blue Harbor Resort & Conference Center Water Park and John Michael Kohler Arts Center in this neighborhood, try to find a hotel near them. Stefanie H. Weill Center for the Performing Arts is another sight that draws the crowds.
What are the top hotels in Downtown Sheboygan?
Inn of Sheboygan and New 3 Bedroom Property In The Heart Of Downtown Sheboygan are among the most popular properties in Downtown Sheboygan. Why not take a look at the amenities and facilities at each and then make up your mind?
How far in advance should I book my Downtown Sheboygan vacation?
Reward yourself with the biggest variety at the lowest prices by booking your trip to Downtown Sheboygan nice and early. Airlines usually sell tickets around a year before departure, so reserve your spot ASAP. That being said, Expedia is dedicated to providing you with the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Downtown Sheboygan travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to build your perfect Downtown Sheboygan package. Once you've made your booking, you can add on the fun stuff like activities and tours. Remember — the more you bundle, the greater the savings!
What should I know before booking a Downtown Sheboygan travel package?
A travel package can be easier on the hip pocket than separately booking everything you need for your getaway. For example, bundle your flights, hotels and rental cars and score big savings. Whatever sort of vacation you're planning, you're bound to find a package that's right for you.
Can I choose my airline with a Downtown Sheboygan Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Downtown Sheboygan vacation package?
Certainly, and we're here to help. You may be able to cancel or amend your Downtown Sheboygan vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If life gets in the way of your vacation, take a look at our Customer Service Portal for more information.

Things to do

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