Title: Sheboygan Vacation Packages & Trips 2025/2026 from CA $1,263 | 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 - ### 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. ![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 $1,263 per person Jan 1 - Jan 5 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Milwaukee (MKE) 19.6/10 Exceptional! (2,425 reviews) What are the best nights rest I’ve ever had. One of the best experiences we’ve had in a hotel in the Midwest. I would recommend rooms on the top floor. Perfectly located downtown Milwaukee. Reviewed on Nov 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-01/2026-01-05/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23253&paandie=true&dealMarker=1WFWn6S80dpBV59SbL8gDIAKj8xnb59UhzawF8Vts8elgYSiKX71Elgc-lkXfajz) ![Potawatomi Hotel & Casino](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/d47b7999_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Potawatomi Hotel & Casino Menomonee River Valley CA $1,563 per person Jan 1 - Jan 5 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Milwaukee (MKE) 18/10 Exceptional! (1,357 reviews) The hotel was beautiful, the room was super clean and the staff were super nice! Very good experience! Reviewed on Nov 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-01/2026-01-05/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8474917&paandie=true&dealMarker=1WFWn6S80dpBV59SbL8gDFuhPJPUP75IkkYLmOQhM8z1YHmfPM1RhCaq29MMUgYM) ![Marriott Milwaukee Downtown](https://images.trvl-media.com/lodging/6000000/5570000/5560600/5560572/3a407323_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Milwaukee Downtown Downtown Milwaukee CA $1,270 per person Jan 1 - Jan 5 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Milwaukee (MKE) 18/10 Exceptional! (697 reviews) The bar was great. The food was awful. Reviewed on Aug 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-01/2026-01-05/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5560572&paandie=true&dealMarker=1WFWn6S80dpBV59SbL8gDIAKj8xnb59UhzawF8Vts8dF4dSTtQxNr-evx_0o09yr) ![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 $1,333 per person Jan 1 - Jan 5 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Milwaukee (MKE) 18.4/10 Exceptional! (1,008 reviews) All was great. Great staff, great room. Would definitely stay there again. Reviewed on Nov 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-01/2026-01-05/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2097106&paandie=true&dealMarker=1WFWn6S80dpBV59SbL8gDHFqYJCrDmbcHwcBKrXlBpFT6-fzdgiZ_d2ZjgkWr4I0) ![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Pfister Hotel Downtown Milwaukee CA $1,319 per person Jan 1 - Jan 5 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Milwaukee (MKE) 19.2/10 Exceptional! (1,786 reviews) I recently stayed at this hotel during a trip to Milwaukee and had a very positive experience overall. The staff was incredibly friendly and attentive from the moment we arrived, which set a great tone for the stay. The property itself—and especially our room—was immaculately clean. Our room had a comfortable bed that made for a great night’s sleep, and we enjoyed a lovely view of the city through the windows. I rated the visit 4 out of 5 stars for two reasons. First, our room was located next to the banquet hall, which happened to be hosting a wedding. While it was fun to see the excitement, we could hear the DJ and music through the walls throughout the evening. Second, the on-site restaurant had poor reviews when it came to gluten-free options, which was disappointing and limited our dining choices. Despite those minor drawbacks, I would absolutely stay at this hotel again on my next visit to Milwaukee. I’d just love to see the restaurant expand its gluten-free offerings to better accommodate guests with dietary needs. Overall, a clean, comfortable, and welcoming place to stay. Reviewed on Nov 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-01/2026-01-05/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19467&paandie=true&dealMarker=1WFWn6S80dpBV59SbL8gDHFqYJCrDmbcHwcBKrXlBpHyed9GaFjhlBuDfmeQoKre) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_6059814) ## 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 $176 CA $200 total Nov 25 - Nov 26 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) Good Reviewed on Nov 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%2F2025&selected=2005043&PinnedHotelID=2005043&HadPinnedHotel=true®ionId=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 $152 CA $173 total Nov 25 - Nov 26 includes taxes & fees 9.6/10 Exceptional! (452 reviews) Did not eat breakfast..staff was very friendly. Room was large, comfortable and clean!! Reviewed on Nov 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%2F2025&selected=83541884&PinnedHotelID=83541884&HadPinnedHotel=true®ionId=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 $109 CA $124 total Dec 1 - Dec 2 includes taxes & fees 8/10 Very Good! (1,000 reviews) Yes- everything was in great order and well kept. Breakfast was outstanding. Reviewed on Nov 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=39976&PinnedHotelID=39976&HadPinnedHotel=true®ionId=6059814) [See all 673 properties in Sheboygan](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F11%2F2025&endDate=26%2F11%2F2025®ionId=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 Arts & Water Segway Tour w/ Private Tour Option](https://mediaim.expedia.com/localexpert/2545922/4b531004-77f8-4c99-8056-0570e577c594.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sheboygan Arts & Water Segway Tour w/ Private Tour Option CA $141 per adult [](https://expedia.ca/things-to-do/sheboygan-arts-water-segway-tour-w-private-tour-option.a2545922.activity-details) ![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 $41 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 $307 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) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars ### Lodging - [Hotels near Blackwolf Run](https://www.expedia.ca/Blackwolf-Run-Hotels.0-l6093963-0.Travel-Guide-Filter-Hotels) - [Hotels near Blue Harbor Resort & Conference Center Water Park](https://www.expedia.ca/Blue-Harbor-Resort-Conference-Center-Water-Park-Hotels.0-l553248621532659437-0.Travel-Guide-Filter-Hotels) - [Farmstay in Cleveland](https://www.expedia.ca/Cleveland-Agritourism.d3000461538-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Cleveland](https://www.expedia.ca/Cleveland-Apart-Hotels.d3000461538-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Cleveland](https://www.expedia.ca/Cleveland-Bed-And-Breakfast.d3000461538-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Cleveland](https://www.expedia.ca/Cleveland-Castles.d3000461538-aaCastles.Travel-Guide-Accommodation) - [Cottages in Cleveland](https://www.expedia.ca/Cleveland-Cottages.d3000461538-aaCottages.Travel-Guide-Accommodation) - [Hostels in Cleveland](https://www.expedia.ca/Cleveland-Hostels.d3000461538-aaHostels.Travel-Guide-Accommodation) - 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[Flights from Minneapolis (MSP) to Sheboygan (SBM)](https://www.expedia.ca/lp/flights/msp/sbm/minneapolis-to-sheboygan) - [Flights from Chicago (ORD) to Sheboygan (SBM)](https://www.expedia.ca/lp/flights/ord/sbm/chicago-to-sheboygan) - [Flights from Savannah (SAV) to Sheboygan (SBM)](https://www.expedia.ca/lp/flights/sav/sbm/savannah-to-sheboygan) - [Flights from Orlando (SFB) to Sheboygan (SBM)](https://www.expedia.ca/lp/flights/sfb/sbm/orlando-to-sheboygan) - [Flights from Edmonton (YXD) to Sheboygan (SBM)](https://www.expedia.ca/lp/flights/yxd/sbm/edmonton-to-sheboygan) ### Packages - [Appleton Vacations](https://www.expedia.ca/Appleton.d6059808.Destination-Travel-Guides) - [Basilica of Saint Josaphat](https://www.expedia.ca/Basilica-Of-Saint-Josaphat-Milwaukee.d6334046.Vacation-Attraction) - [Belgium Vacations](https://www.expedia.ca/Belgium.d184176.Destination-Travel-Guides) - [Blue Harbor Resort & Conference Center Water Park](https://www.expedia.ca/Blue-Harbor-Resort-Conference-Center-Water-Park-Sheboygan.d553248621532659437.Vacation-Attraction) - [Brookfield Square Mall](https://www.expedia.ca/Brookfield-Square-Mall-Milwaukee.d6333105.Vacation-Attraction) - [Brookfield Vacations](https://www.expedia.ca/Brookfield.d7083.Destination-Travel-Guides) - [Cabela's](https://www.expedia.ca/Cabelas-Richfield.d553248621532659426.Vacation-Attraction) - [Cleveland Vacations](https://www.expedia.ca/Cleveland.d3000461538.Destination-Travel-Guides) - [Discovery World](https://www.expedia.ca/Discovery-World-East-Town.d6068283.Vacation-Attraction) - [Erin Hills Golf Course](https://www.expedia.ca/Erin-Hills-Golf-Course-Hartford.d6181490.Vacation-Attraction) - [Harley Davidson Factory](https://www.expedia.ca/Harley-Davidson-Factory-Milwaukee.d6334034.Vacation-Attraction) - [Harley-Davidson Museum](https://www.expedia.ca/Harley-Davidson-Museum-Milwaukee.d6279040.Vacation-Attraction) - [Jackson Vacations](https://www.expedia.ca/Jackson.d602318.Destination-Travel-Guides) - [Visit Johnsonville](https://www.expedia.ca/Johnsonville.dx553248635975866500) - [Kimberly Vacations](https://www.expedia.ca/Kimberly.d181436.Destination-Travel-Guides) - [Mequon Vacations](https://www.expedia.ca/Mequon.d8809.Destination-Travel-Guides) - [Milwaukee Art Museum](https://www.expedia.ca/Milwaukee-Art-Museum-East-Town.d6068277.Vacation-Attraction) - [Milwaukee City Hall](https://www.expedia.ca/Milwaukee-City-Hall-Downtown-Milwaukee.d6068275.Vacation-Attraction) - [Milwaukee Public Library](https://www.expedia.ca/Milwaukee-Public-Library-Westown.d6068293.Vacation-Attraction) - [Milwaukee Vacations](https://www.expedia.ca/Milwaukee.d602647.Destination-Travel-Guides) - [Mitchell Park Horticultural Conservatory](https://www.expedia.ca/Mitchell-Park-Horticultural-Conservatory-Milwaukee.d6068291.Vacation-Attraction) - [Oostburg Vacations](https://www.expedia.ca/Oostburg.d3000461927.Destination-Travel-Guides) - [Visit Oostburg](https://www.expedia.ca/Oostburg.dx3000461927) - [Oshkosh Vacations](https://www.expedia.ca/Oshkosh.d2699.Destination-Travel-Guides) - [Pettit National Ice Center](https://www.expedia.ca/Pettit-National-Ice-Center-Milwaukee.d6335062.Vacation-Attraction) - [Potawatomi Bingo Casino](https://www.expedia.ca/Potawatomi-Bingo-Casino-Milwaukee.d6335076.Vacation-Attraction) - [Shalom Wildlife](https://www.expedia.ca/Shalom-Wildlife-West-Bend.d6335542.Vacation-Attraction) - [Skip Barber Driving School](https://www.expedia.ca/Skip-Barber-Driving-School-Plymouth.d553248621532659327.Vacation-Attraction) - [The Bull at Pinehurst Farms Golf Course](https://www.expedia.ca/The-Bull-At-Pinehurst-Farms-Golf-Course-Sheboygan-Falls.d6199618.Vacation-Attraction) - [Washington County Fair Grounds](https://www.expedia.ca/Washington-County-Fair-Grounds-West-Bend.d6181503.Vacation-Attraction) - [Whitefish Bay Vacations](https://www.expedia.ca/Whitefish-Bay.d6335560.Destination-Travel-Guides) - [Wisconsin Vacations](https://www.expedia.ca/Wisconsin.d251.Destination-Travel-Guides) ### Cars - [Car rental Kohler](https://www.expedia.ca/Car-Rentals-In-Kohler.d8176.Car-Rental-Guide) - 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