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.
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
Downtown Kenosha
per person
Jun. 26 - Jun. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.4/10 Exceptional! (1,000 reviews)
Beautifully restored historic building, very charming. But there was no drive up/drop off capability. So you had to drop your things off on the sidewalk and park elsewhere, then carry everything up the stairs into the lobby.

Reviewed on Mar. 9, 2025

Brew City Game Room Fenced Yard Sleeps 13

Brew City Game Room Fenced Yard Sleeps 13

2 out of 5
Wauwatosa
per person
May 16 - May 19
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
No reviews
Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
per person
May 16 - May 19
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Milwaukee (MKE)
9.6/10 Exceptional! (250 reviews)
The property was clean and spacious and a convenient location to enjoy my first March Madness NCAA tourney in person! Near good food and a Crossfit gym, too!

Reviewed on Mar. 25, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
per person
Jun. 13 - Jun. 15
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Milwaukee (MKE)
9.8/10 Exceptional! (2,278 reviews)
Very beautiful, plenty of art, clean and a few real nice restaurants/bars in the hotel

Reviewed on Apr. 10, 2025

Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
per person
Jun. 20 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Milwaukee (MKE)
9/10 Wonderful! (1,003 reviews)
Great place for a family getaway!

Reviewed on Apr. 1, 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 $93 per night from Apr. 13 to Apr. 14
CA $93
CA $106 total
includes taxes & fees
Apr 13 - Apr 14
7.2/10 Good! (344 reviews)
"Staff are very pleasant,the room was clean.."

Reviewed on Apr. 5, 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 $131 per night from Apr. 18 to Apr. 19
CA $131
CA $148 total
includes taxes & fees
Apr 18 - Apr 19
8.6/10 Excellent! (876 reviews)
"Thank you"

Reviewed on Apr. 4, 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 $114 per night from Apr. 27 to Apr. 28
CA $114
CA $130 total
includes taxes & fees
Apr 27 - Apr 28
9.2/10 Wonderful! (597 reviews)
Great place
"It was a great stay will be staying there again"

Reviewed on Apr. 7, 2025

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 704 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?
Offering great value package deals from CA $706 on Expedia, you’ll be thrilled with how little a vacation to Pleasant Prairie costs! Expedia’s packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Pleasant Prairie?
If you’re looking to score a cheap Pleasant Prairie vacation package, consider planning a trip in February, November and December. You’re likely to find lower prices on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Pleasant Prairie?
The ideal duration of your Pleasant Prairie vacation depends on what you’d like to see and do. Typically, a few days to a week will give you enough time to hit all the leading attractions and discover some hidden spots along the way.
How to find the best Pleasant Prairie package deals?
Use Expedia’s filters to help you find some terrific Pleasant Prairie package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or look for Pleasant Prairie package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package well in advance.
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, flight and hotel into one great-value price and you could save hundreds of dollars. You’ll typically land a better deal than booking each component individually. And you’ll still enjoy the flexibility to create a personalized Pleasant Prairie vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Pleasant Prairie?
If you’ve got your Pleasant Prairie travel dates confirmed, book early to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Pleasant Prairie?

  1. Choose when to get away: Check your diary and get packing. Your favorite time of year and the activities available will also help you decide when to vacation in Pleasant Prairie.
  2. Set a budget: Factor in costs like flights, meals and transportation when calculating how much to set aside for your trip to Pleasant Prairie. Then, select a hotel that works with your budget, whether that’s an affordable option or a swankier getaway.
  3. Decide your trip length: Consider how long you want to spend discovering Pleasant Prairie. Plan your days so you can get to all the experiences and attractions you’re interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized 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.