Title: Pleasant Prairie Vacation Packages & Trips 2026 from CA $948 | Expedia.ca [Hotels in Pleasant Prairie](https://expedia.ca/Pleasant-Prairie-Hotels.d180854.Travel-Guide-Hotels)[Vacation Rentals in Pleasant Prairie](https://expedia.ca/Pleasant-Prairie-Vacation-Rentals.d180854.Travel-Guide-VacationRentals)[Pleasant Prairie Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Prairie.d180854.Car-Rental-Guide) ![](https://images.trvl-media.com/place/180854/e52e064a-8ac0-4f10-9116-feda6e6ff45f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pleasant Prairie Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Pleasant Prairie Vacation With plenty of highlights as well as hidden gems, this city is best experienced with a Pleasant Prairie vacation package. Find somewhere to stay in Camp Lake, which is great for fishing, walking and camping. Make your trip to Pleasant Prairie even more fun by going sightseeing. [Pleasant Prairie RecPlex](https://www.expedia.ca/Pleasant-Prairie-RecPlex-Pleasant-Prairie.d6335451.Vacation-Attraction), [Pleasant Prairie Premium Outlets](https://www.expedia.ca/Pleasant-Prairie-Premium-Outlets-Pleasant-Prairie.d6335447.Vacation-Attraction) and [Americas Action Territory Family Fun Park](https://www.expedia.ca/Americas-Action-Territory-Family-Fun-Park-Kenosha.d6334005.Vacation-Attraction) are some of the top attractions you'll want to explore. A few clicks is all it takes to build your perfect Pleasant Prairie vacation on Expedia. ## Top Pleasant Prairie Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $948 per person Mar 26 - Mar 31 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) 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 $1,236 per person Mar 26 - Mar 31 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Milwaukee (MKE) 9.2/10 Wonderful! (1,008 reviews) Staff was great and helpful, food was delicious and the room was amazing! Reviewed on Feb 9, 2026 ![Holiday Inn Express Milwaukee Downtown by IHG](https://images.trvl-media.com/lodging/58000000/57140000/57132500/57132464/ecb2f8b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Milwaukee Downtown by IHG Downtown Milwaukee CA $1,038 per person Mar 26 - Mar 31 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Milwaukee (MKE) 9/10 Wonderful! (1,002 reviews) Room was good for the price however housecleaning was hit or miss and they did not clean the bathroom floor once in the 5 days we were there and on the days they did clean the room, they would forget to empty out the trash cans or left the bathroom sink dirty. Breakfast was just ok, nothing to rave about. The staff day staff was much more helpful than the night staff but both were friendly. The hotel itself is nice and centrally located. We walked almost everywhere. Reviewed on Jan 27, 2026 ![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 $1,033 per person Mar 26 - Mar 31 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Milwaukee (MKE) 9/10 Wonderful! (1,357 reviews) Room was clean and beautiful!! Front desk staff was helpful and has one of the best selections of slot machines in the casino will definitely be going back!!! Reviewed on Feb 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 $1,315 per person Mar 26 - Mar 31 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Milwaukee (MKE) 9.4/10 Exceptional! (1,001 reviews) Clean room. Greeted with a free beer! Reviewed on Feb 8, 2026 ## Ready to book your vacation to Pleasant Prairie? Choose your dates ## Pleasant Prairie Hotel Deals ![Days Inn by Wyndham Pleasant Prairie Kenosha](https://images.trvl-media.com/lodging/1000000/40000/40000/39969/883bb863_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Pleasant Prairie Kenosha 7540 118th Ave Pleasant Prairie WI Fully refundableReserve now, pay when you stay CA $92 CA $104 total Feb 12 - Feb 13 includes taxes & fees 8.2/10 Very Good! (398 reviews) Staff were friendly and helpful. Room was clean and comfortable. Fridge was either too warm or freezing the food. Forgot to tell them. For the first 2 nights I just had the sheet and the top sheet but when I asked they gave me a comforter. Coffee was terrible. Hot breakfast was good but the same ... Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=39969&PinnedHotelID=39969&HadPinnedHotel=true®ionId=180854) ![Doubletree by Hilton Pleasant Prairie Kenosha](https://images.trvl-media.com/lodging/1000000/110000/105200/105109/0d8dd0dd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Doubletree by Hilton Pleasant Prairie Kenosha 11800 108th St Pleasant Prairie WI Fully refundableReserve now, pay when you stay CA $125 CA $142 total Mar 1 - Mar 2 includes taxes & fees 8.6/10 Excellent! (965 reviews) Room was very big and nice. The hot tub and pool were also very nice. Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=105109&PinnedHotelID=105109&HadPinnedHotel=true®ionId=180854) ![Fairfield Inn & Suites Kenosha Pleasant Prairie](https://images.trvl-media.com/lodging/30000000/29510000/29509200/29509196/8af60f68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fairfield Inn & Suites Kenosha Pleasant Prairie 10601 120TH AVENUE Pleasant Prairie WI Fully refundableReserve now, pay when you stay CA $133 CA $150 total Feb 15 - Feb 16 includes taxes & fees 9.2/10 Wonderful! (692 reviews) The place was clean and well maintained. We appreciate how they have some little complimentary drinks for guests. The breakfast was good and fair. The staff were also accommodating and nice! Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=29509196&PinnedHotelID=29509196&HadPinnedHotel=true®ionId=180854) [See all 795 properties in Pleasant Prairie](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026®ionId=180854) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app