Pleasant Prairie Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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, Pleasant Prairie Premium Outlets and Americas Action Territory Family Fun Park 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.
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,109, price is now CA $949 per person
CA $949
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,385 reviews)
Manager checked in on us personally! Beds were comfortable! Wished there was coffee in rooms instead of hallway.

Reviewed on Aug. 15, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was CA $1,224, price is now CA $1,000 per person
CA $1,000
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Such a cool place! The room was spacious and clean, and it was a great location for exploring the city. Staff were super friendly, and the food and vibe of the restaurant were great!

Reviewed on Aug. 21, 2025

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $1,258, price is now CA $1,058 per person
CA $1,058
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (287 reviews)
Room was great, location was great. Easy check in. Accessible room. Only negative was I only had extremely hot water until my last day. They offered me a different room but it wasn’t as good as the one I was in so I stayed. I was totally fine with the hot water because the room itself was amazing I would go back and stay here again/

Reviewed on Aug. 16, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,190, price is now CA $1,004 per person
CA $1,004
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.6/10 Exceptional! (1,698 reviews)
Beautiful building and great service

Reviewed on Aug. 16, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was CA $1,215, price is now CA $1,034 per person
CA $1,034
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9/10 Wonderful! (1,340 reviews)
People visting the property were not friendly.

Reviewed on Aug. 20, 2025

Ready to book your vacation to Pleasant Prairie?

 

Choose your dates

Pleasant Prairie Hotel Deals

Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha

2.5 out of 5
7540 118th Ave, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Sep 21 to Sep 22
CA $98
CA $111 total
Sep 21 - Sep 22
includes taxes & fees
7.2/10 Good! (438 reviews)
"It was just ok. Picked this place because it was close to where we needed to be. Room was clean and breakfast was ok. Would recommend."

Reviewed on Aug. 18, 2025

Days Inn by Wyndham Pleasant Prairie Kenosha
Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

4 out of 5
11800 108th St, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Sep 14 to Sep 15
CA $142
CA $162 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (920 reviews)
"We always stay here when visiting the Renaissance Faire. Had a great time!"

Reviewed on Aug. 19, 2025

Doubletree by Hilton Pleasant Prairie Kenosha
Fairfield Inn & Suites Kenosha Pleasant Prairie

Fairfield Inn & Suites Kenosha Pleasant Prairie

2.5 out of 5
10601 120TH AVENUE, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Sep 14 to Sep 15
CA $139
CA $158 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (638 reviews)
"It was good"

Reviewed on Aug. 9, 2025

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 712 properties in Pleasant Prairie
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 Pleasant Prairie vacation package cost?
You'll find cheap prices from CA $949 on Expedia for your Pleasant Prairie escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Pleasant Prairie costs.
What are the cheapest months to go to Pleasant Prairie?
If you're hoping to score a cheap Pleasant Prairie vacation package, consider visiting in February, November and December. You'll usually find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Pleasant Prairie?
Usually, a handful of days is enough to tick off the main attractions during your Pleasant Prairie vacation. But if you want to have more time to chill out or go on day trips, think about extending your itinerary.
How to find the best Pleasant Prairie package deals?
Bagging a cheap Pleasant Prairie package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most wallet-friendly Pleasant Prairie package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Pleasant Prairie vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Pleasant Prairie vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Pleasant Prairie?
If you've got your Pleasant Prairie vacation dates finalized, book as early as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Pleasant Prairie?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Pleasant Prairie.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Pleasant Prairie.
  3. Decide how long to go away for: Now that you're more familiar with Pleasant Prairie, you can work out the perfect length of your vacation. Create a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Pleasant Prairie vacation package.

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