Pleasant Prairie Vacations from $264

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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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was $330, price is now $264 per person
$264
per person
Jan 26 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
Breakfast was advertised as free but it was $15

Reviewed on Dec 7, 2025

Antioch Hotel & Suites

Antioch Hotel & Suites

3 out of 5
Price was $582, price is now $459 per person
$459
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9/10 Wonderful! (454 reviews)
Nice room and very friendly staff.

Reviewed on Nov 30, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $675, price is now $547 per person
$547
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Did not try breakfast!

Reviewed on Dec 11, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $576, price is now $471 per person
$471
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $665, price is now $553 per person
$553
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Great ambiance! Loved the view from our room too.

Reviewed on Dec 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
$66 nightly
The price is $75 total per night from Dec 14 to Dec 15
$75 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (351 reviews)
Everything was as expected! I will certainly consider this location again

Reviewed on Dec 8, 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
$98 nightly
The price is $111 total per night from Dec 28 to Dec 29
$111 total
Dec 28 - Dec 29
Total with taxes and fees
8.6/10 Excellent! (953 reviews)
Staff, room condition, attached restaurant, and location were all perfect!

Reviewed on Nov 24, 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 Dec 21 to Dec 22
$110 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (671 reviews)
Close to Pleasant Prairie Outlets

Reviewed on Dec 5, 2025

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 790 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.

Find the Best Pleasant Prairie Vacation Packages

Pleasant Prairie Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Population
20,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Simmons Island Beach, Kenosha Public Museum and Americas Action Territory Family Fun Park

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Frequently asked questions

How much does a Pleasant Prairie vacation package cost?
Offering great value package deals from $264 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.

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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.