Pleasant Prairie Vacation Packages

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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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was CA $859, price is now CA $685 per person
CA $685
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
8.4/10 Very Good! (1,002 reviews)
It was a wonderful experience. The staff was super friendly and kind. We found it kid friendly and felt safe.

Reviewed on Aug. 15, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was CA $1,225, price is now CA $974 per person
CA $974
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Amazing night front desk staff!

Reviewed on Aug. 26, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was CA $1,430, price is now CA $1,166 per person
CA $1,166
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9/10 Wonderful! (1,340 reviews)
The rooms are very nice and clean. I liked that they had adjoining rooms for two families. Easy uber picked to go to Summerfest grounds.

Reviewed on Aug. 25, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,172, price is now CA $964 per person
CA $964
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.6/10 Exceptional! (1,698 reviews)
This is a great property to stay at, the hotel is very nice with lots of artwork and ambience. I highly recommend if you’re ever in Milwaukee..

Reviewed on Aug. 23, 2025

Hilton Garden Inn Milwaukee Airport

Hilton Garden Inn Milwaukee Airport

3 out of 5
Price was CA $900, price is now CA $745 per person
CA $745
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,001 reviews)
Beds were so comfortable. Rooms spacious and clean. All of the workers were super nice! Definetly would stay again.

Reviewed on Aug. 10, 2025

Ready to book your vacation to Pleasant Prairie?

 

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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 $122 per night from Sep 21 to Sep 22
CA $122
CA $139 total
Sep 21 - Sep 22
includes taxes & fees
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 $159 per night from Sep 7 to Sep 8
CA $159
CA $181 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (923 reviews)
"Convenient close to shops"

Reviewed on Aug. 22, 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 $134 per night from Sep 14 to Sep 15
CA $134
CA $152 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (639 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
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Frequently asked questions

How much does a Pleasant Prairie vacation package cost?
You'll find cheap prices from CA $685 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.