Title: Sheboygan Vacation Packages & Trips 2026 from CA $847 | Expedia.ca

[Hotels in Sheboygan](https://expedia.ca/Sheboygan-Hotels.d6059814.Travel-Guide-Hotels)[Vacation Rentals in Sheboygan](https://expedia.ca/Sheboygan-Vacation-Rentals.d6059814.Travel-Guide-VacationRentals)[Flights to Sheboygan](https://expedia.ca/Cheap-Flights-To-Sheboygan.d6059814.Travel-Guide-Flights)[Sheboygan Car Rentals](https://expedia.ca/Car-Rentals-In-Sheboygan.d6059814.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6059814/9f080f00-14ec-4ba6-b20b-e1e9ca009a99.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Sheboygan Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Gene LeSage

- ##  
Plan, book, travel with confidence
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### 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](https://www.expedia.ca/Blue-Harbor-Resort-Conference-Center-Water-Park-Sheboygan.d553248621532659437.Vacation-Attraction), [Kohler Design Center](https://www.expedia.ca/Kohler-Design-Center-Kohler.d553248621532659431.Vacation-Attraction) and [John Michael Kohler Arts Center](https://www.expedia.ca/John-Michael-Kohler-Arts-Center-Downtown-Sheboygan.d6224268.Vacation-Attraction). 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.

![Sheraton Milwaukee Brookfield Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9488/ac547b1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sheraton Milwaukee Brookfield Hotel

CA $847

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

8.4/10 Very Good! (500 reviews)

Wonderful stay, clean room, friendly staff, lots of shopping near by

Reviewed on Jan 9, 2026

![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Saint Kate - The Arts Hotel

Downtown Milwaukee

CA $1,109

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.8/10 Exceptional! (2,425 reviews)

Great hotel! So fun and unique. Very clean and personalized

Reviewed on Jan 11, 2026

![Kinn Guesthouse Bay View](https://images.trvl-media.com/lodging/21000000/20240000/20233300/20233264/4e3a3faa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kinn Guesthouse Bay View

Bay View

CA $1,009

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.6/10 Exceptional! (428 reviews)

The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Iron Horse Hotel

Fifth Ward

CA $1,153

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.2/10 Wonderful! (1,008 reviews)

Room ready early. Everything clean and well-kept. Will stay there again.

Reviewed on Jan 7, 2026

![The Brewhouse Inn & Suites](https://images.trvl-media.com/lodging/8000000/7090000/7084400/7084340/c5b60965_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Brewhouse Inn & Suites

Westown

CA $1,008

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.4/10 Exceptional! (1,001 reviews)

It would be very helpful clean daily the room

Reviewed on Jan 10, 2026

## Ready to book your vacation to Sheboygan?

Choose your dates

## Sheboygan Hotel Deals

![Grandstay Residential Suites Hotel - Sheboygan](https://images.trvl-media.com/lodging/3000000/2010000/2005100/2005043/402d6f8a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Grandstay Residential Suites Hotel - Sheboygan

708 Niagara Avenue Sheboygan WI

Fully refundableReserve now, pay when you stay

CA $174

CA $197 total

Jan 13 - Jan 14

includes taxes & fees

8.6/10 Excellent! (1,015 reviews)

Room was very spacious. 2 bedrooms bed and pillows comfortable. Staff was nice for check in. Breakfast was adequate. As mentioned before hot plate was cold but there is a microwave to heat up your food. Place was clean. Walking distance to restaurants

Reviewed on Dec 22, 2025

[](https://expedia.ca/Hotel-Search?startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&selected=2005043&PinnedHotelID=2005043&HadPinnedHotel=true&regionId=6059814)

![Watershed Hotel](https://images.trvl-media.com/lodging/84000000/83550000/83541900/83541884/521022c3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Watershed Hotel

838 N 15th St Sheboygan WI

Fully refundableReserve now, pay when you stay

CA $150

CA $171 total

Jan 13 - Jan 14

includes taxes & fees

9.6/10 Exceptional! (472 reviews)

Friendly, professional staff. Clean and spacious room.

Reviewed on Dec 28, 2025

[](https://expedia.ca/Hotel-Search?startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&selected=83541884&PinnedHotelID=83541884&HadPinnedHotel=true&regionId=6059814)

![La Quinta Inn by Wyndham Sheboygan](https://images.trvl-media.com/lodging/1000000/40000/40000/39976/0c381b2f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn by Wyndham Sheboygan

2932 Kohler Memorial Dr Sheboygan WI

Fully refundableReserve now, pay when you stay

CA $107

CA $121 total

Jan 18 - Jan 19

includes taxes & fees

8/10 Very Good! (1,000 reviews)

Rooms were clean, for the price,well worth it, my only complaint,it's not La Quinta's fault, was all the smokers smoking in there rooms and hovering around the exit doors smoking

Reviewed on Jan 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=39976&PinnedHotelID=39976&HadPinnedHotel=true&regionId=6059814)

[See all 675 properties in Sheboygan](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&regionId=6059814)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### 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. 

[](https://expedia.ca/Blue-Harbor-Resort-Conference-Center-Water-Park-Sheboygan.d553248621532659437.Vacation-Attraction)

### What to do in Sheboygan

![Sheboygan Showdown Scavenger Hunt](https://mediaim.expedia.com/localexpert/46890486/dc46a650-8967-44ff-992c-00c6ce0ccf4f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sheboygan Showdown Scavenger Hunt

CA $40

per adult

[](https://expedia.ca/things-to-do/sheboygan-showdown-scavenger-hunt.a46890486.activity-details)

![Private Professional Golf Experience in American Club Wisconsin](https://mediaim.expedia.com/localexpert/49186912/b820446d-7032-45ed-8c64-ffd1c8cfc2ff.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Private Professional Golf Experience in American Club Wisconsin

CA $304

per adult

[](https://expedia.ca/things-to-do/private-professional-golf-experience-in-american-club-wisconsin.a49186912.activity-details)

[See all activities in Sheboygan](https://expedia.ca/things-to-do/search?rid=6059814)

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- [Whitefish Bay Vacations ](https://www.expedia.ca/Whitefish-Bay.d6335560.Destination-Travel-Guides)
- [Wisconsin Vacations ](https://www.expedia.ca/Wisconsin.d251.Destination-Travel-Guides)

- [Car rental Kohler ](https://www.expedia.ca/Car-Rentals-In-Kohler.d8176.Car-Rental-Guide)
- [Car rental Sheboygan Falls ](https://www.expedia.ca/Car-Rentals-In-Sheboygan-Falls.d55959.Car-Rental-Guide)
- [Hertz Rental Cars in Sheboygan Falls ](https://www.expedia.ca/Hertz-Car-Rentals-In-Sheboygan-Falls.d55959-c40.Car-Rental-Guide-Suppliers)
- [Suv Car Rentals in Kohler ](https://www.expedia.ca/SUV-Car-Rentals-In-Kohler.d8176-tSUV.Car-Rental-Guide-Class)

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

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