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.
Landing Apartments at Mayfair Collection

Landing Apartments at Mayfair Collection

4 out of 5
Wauwatosa
Price was CA $1,799, price is now CA $1,617 per person
CA $1,617
per person
Aug 28 - Aug 31
found 18 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
10/10 Exceptional! (4 reviews)
Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!

Reviewed on May 21, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,746, price is now CA $1,836 per person
CA $1,836
per person
Aug 28 - Aug 31
found 18 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Staff were extremely friendly and helpful!

Reviewed on Jul 4, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,967, price is now CA $1,655 per person
CA $1,655
per person
Aug 28 - Aug 31
found 18 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.8/10 Exceptional! (2,645 reviews)
Great location. The staff was very kind. Cool room

Reviewed on Jul 3, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,978, price is now CA $1,687 per person
CA $1,687
per person
Aug 28 - Aug 31
found 18 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,176 reviews)
Beautiful property! I like the outdoor bar and restaurant on site. Rooms are very nice and very clean!. Comfortable beds.

Reviewed on Jul 4, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $2,042, price is now CA $1,847 per person
CA $1,847
per person
Aug 28 - Aug 31
found 18 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.4/10 Exceptional! (369 reviews)
Loved our stay! And want to go back!

Reviewed on Jun 30, 2026

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 $108 per night from Jul 5 to Jul 6
CA $108
CA $123 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very good! (493 reviews)
"Everything was meh. Nothing was great."

Reviewed on Jul 3, 2026

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 $163 per night from Jul 26 to Jul 27
CA $163
CA $185 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Clean room, friendly service, excellent location"

Reviewed on Jul 4, 2026

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

Fairfield Inn & Suites Kenosha Pleasant Prairie

3 out of 5
10601 120TH AVENUE Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Jul 26 to Jul 27
CA $168
CA $190 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (724 reviews)
"Great customer service, food and the property was very clean. The pool was out of service."

Reviewed on Jun 30, 2026

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 804 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.
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Stay near popular Pleasant Prairie attractions

Pleasant Prairie Premium Outlets

9.0/10 (385 reviews)
During your trip to Pleasant Prairie, you can do some window-shopping at Pleasant Prairie Premium Outlets. Wander the lakeside in this family-friendly area.
See properties

Frequently asked questions

How much does a Pleasant Prairie vacation package cost?
You'll find cheap prices from CA $1,617 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.

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