Pleasant Prairie Vacations from $366

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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.

The Latest Pleasant Prairie vacation packages

Price found within the past 48 hours. Click for updated prices.
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
Price was $456, price is now $366 per person
$366
per person
Oct 22 - Oct 25
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Milwaukee (MKE)
8.6/10 Excellent! (1,511 reviews)
With any issue that may have raised. The staff was quick to resolve and or offer a discount.

Reviewed on Sep 17, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $1,220, price is now $928 per person
$928
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9.8/10 Exceptional! (2,411 reviews)
What a great property! The staff was super friendly, helpful and accommodating. The Expedia VIP benefit was given up-front without me having to ask for it. The property itself was exceptionally well-kept. The location is amazing. Downtown Milwaukee is super walkable (in the right season, depending on your tolerance to cold weather) and this property is pretty much central to everything you could want! Will stay again. A+++

Reviewed on Sep 15, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,559, price is now $1,226 per person
$1,226
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9.6/10 Exceptional! (1,736 reviews)
Staff, protery, along with the entire experience was absolute excellence.

Reviewed on Sep 17, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $1,041, price is now $820 per person
$820
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9/10 Wonderful! (1,362 reviews)
All was excellent- can’t wait to go back

Reviewed on Sep 18, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $886, price is now $711 per person
$711
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9.6/10 Exceptional! (410 reviews)
The house was spacious and well equipped the downstairs restaurant was great. The stairs up to the guest rooms were reminiscent of Europe where elevators are scarce

Reviewed on Sep 10, 2025

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Discover the most popular places to visit in Pleasant Prairie

Pleasant Prairie Premium Outlets

4.5/5(196 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.

Pleasant Prairie Premium Outlets

Pleasant Prairie RecPlex

4.5/5(47 reviews)

Catch an event at Pleasant Prairie RecPlex during your trip to Pleasant Prairie. Wander the lakeside in this family-friendly area.

Pleasant Prairie RecPlex

Jelly Belly Center

Take the family on an outing to Jelly Belly Center during your trip to Pleasant Prairie. While you're in the area, stroll along the lakeside.

Jelly Belly Center

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
$76 nightly
The price is $86 total per night from Sep 22 to Sep 23
$86 total
Sep 22 - Sep 23
Total with taxes and fees
8.2/10 Very Good! (316 reviews)
"It was difficult to close the room door. It was _impossible_ to close the bathroom door: it was bigger than the jamb that it was supposed to fit into. In the sink area, the screw that held the coffee-maker's electrical cord in place in the outlet box overlapped the light switch so that it was difficult ..."

Reviewed on Sep 3, 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
$122 nightly
The price is $139 total per night from Oct 12 to Oct 13
$139 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (926 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
$97 nightly
The price is $110 total per night from Oct 12 to Oct 13
$110 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (643 reviews)
"The staff was very nice and always friendly. Alexis checked us in a day earlier then when we were to arrive and was very helpful and such a great peraon to talk to. The property is always nice and clean and is close to and Outlet mall which makes it fun to goto and shop."

Reviewed on Sep 9, 2025

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 743 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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Frequently asked questions

How much does a Pleasant Prairie vacation package cost?
Offering great value package deals from $366 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?
January, February and November are the best times to look for cheap Pleasant Prairie vacation packages. Traveling in less busy months means you can generally find reduced prices on accommodations and flights.
How many days is enough for Pleasant Prairie?
Typically, a handful of days is enough to check out the top sights during your Pleasant Prairie vacation. But if you'd like to have more time to chill out or take day trips, think about extending your trip.
Is it worth booking a vacation package to Pleasant Prairie?
Pleasant Prairie is a good vacation destination with attractions like Pleasant Prairie RecPlex among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Pleasant Prairie vacation promises a good time for everyone.
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.
Does Expedia offer Book Now, Pay Later Pleasant Prairie vacation packages?
Set off on your dream escape to Pleasant Prairie with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up travel deals before they sell out.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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