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.
Delavan Inn and Suites

Delavan Inn and Suites

2 out of 5
Price was CA $531, price is now CA $511 per person
CA $511
per person
Oct 23 - Oct 26
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
6.2/10 (859 reviews)
No extra pillows and no extra comforter I got charged extra person but don’t get the extra necessities for the extra person would like a refund for that extra person overall breakfast could use a upgrade it was not overall good

Reviewed on Sep. 3, 2025

Antioch Hotel & Suites

Antioch Hotel & Suites

3 out of 5
Price was CA $696, price is now CA $638 per person
CA $638
per person
Oct 23 - Oct 26
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9/10 Wonderful! (400 reviews)
The room was small and dirty. The pool and hot tub area was nice and clean. Breakfast was fine.

Reviewed on Sep. 1, 2025

Courtyard by Marriott Milwaukee Brookfield at Poplar Creek

Courtyard by Marriott Milwaukee Brookfield at Poplar Creek

3 out of 5
Price was CA $866, price is now CA $821 per person
CA $821
per person
Oct 10 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.6/10 Excellent! (71 reviews)
Okay hotel, when I booked they said there was a microwave in room but there wasn’t. Staff was rude and uninformative

Reviewed on Sep. 1, 2025

avid hotel Oak Creek by IHG

avid hotel Oak Creek by IHG

2.5 out of 5
Price was CA $831, price is now CA $793 per person
CA $793
per person
Oct 10 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.8/10 Exceptional! (131 reviews)
What a beautiful place! And we got such a warm welcome when we checked in.

Reviewed on Sep. 6, 2025

Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

4 out of 5
Price was CA $917, price is now CA $890 per person
CA $890
per person
Oct 10 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.8/10 Excellent! (925 reviews)
Convenient close to shops

Reviewed on Aug. 22, 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
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Sep 14 to Sep 15
CA $156
CA $177 total
Sep 14 - Sep 15
includes taxes & fees
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 $87 per night from Oct 5 to Oct 6
CA $87
CA $99 total
Oct 5 - Oct 6
includes taxes & fees
Wingate by Wyndham Sheboygan
Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43

2.5 out of 5
4332 N 40th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Sep 14 to Sep 15
CA $105
CA $119 total
Sep 14 - Sep 15
includes taxes & fees
Quality Inn Sheboygan North I-43
See all 464 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Downtown Sheboygan vacation package cost?
Starting from as little as CA $511, 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

Sheboygan Showdown Scavenger Hunt

Sheboygan Showdown Scavenger Hunt

CA $40
per adult
Sheboygan Showdown Scavenger Hunt
Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Arts & Water Segway Tour w/ Private Tour Option

CA $139
per adult
Sheboygan Arts & Water Segway Tour w/ Private Tour Option
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.