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 Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
per person
Apr. 19 - Apr. 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,004 reviews)
Staff was great for the hotel.

Reviewed on Mar. 3, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.8/10 Exceptional! (2,159 reviews)
Fantastic location, gorgeous hotel, wonderful staff!

Reviewed on Mar. 1, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
per person
May 5 - May 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.6/10 Exceptional! (367 reviews)
I had no idea that I’d find such a wonderful option for my needs. It felt like home away from home, which is very important to me. I’ll be back soon!

Reviewed on Jan. 16, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
per person
Apr. 19 - Apr. 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,612 reviews)
Layla and Rishav were lovely at check in making sure our room was exactly what we wanted. we stayed in a wonderful quiet room on the 8 th floor in the historic part of the hotel. Dinner at the Mason Grill also perfect ! We can’t wait to come back.

Reviewed on Mar. 3, 2025

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
per person
May 5 - May 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.2/10 Wonderful! (114 reviews)
Rachel was super helpful and kind. Our room was beautiful and clean. I really loved the organic lavender lotion from a local vendor. Great stay!

Reviewed on Sep. 30, 2024

Ready to book your vacation to Pleasant Prairie?

 

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Pleasant Prairie Hotel Deals

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 Mar. 23 to Mar. 24
CA $159
CA $180 total
includes taxes & fees
Mar 23 - Mar 24
8.6/10 Excellent! (865 reviews)
"Check in process was a breeze and the warm cookie made it that much better"

Reviewed on Feb. 23, 2025

Doubletree by Hilton Pleasant Prairie Kenosha
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 $86 per night from Mar. 16 to Mar. 17
CA $86
CA $97 total
includes taxes & fees
Mar 16 - Mar 17
7.2/10 Good! (309 reviews)
"Everything was fine"

Reviewed on Feb. 22, 2025

Days Inn by Wyndham 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 $118 per night from Mar. 9 to Mar. 10
CA $118
CA $134 total
includes taxes & fees
Mar 9 - Mar 10
9.2/10 Wonderful! (584 reviews)
"Excellent facility and staff"

Reviewed on Feb. 28, 2025

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 715 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 $769 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.