Pleasant Prairie Vacations from $579

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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.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Avenues West
Price was $687, price is now $579 per person
$579
per person
Dec 28 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9/10 Wonderful! (1,417 reviews)

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $816, price is now $617 per person
$617
per person
Dec 28 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $1,364, price is now $1,054 per person
$1,054
per person
Dec 28 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.4/10 Exceptional! (444 reviews)
great staff

Reviewed on Oct 27, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $796, price is now $650 per person
$650
per person
Dec 28 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.4/10 Exceptional! (508 reviews)

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $794, price is now $661 per person
$661
per person
Nov 28 - Nov 30
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
Clean rooms, top floor pool, easy in/out parking, great gym, helpful staff & beautiful architecture.

Reviewed on Oct 26, 2026

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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.
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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
$53 nightly
The price is $60 total per night from Nov 8 to Nov 9
$60 total
Nov 8 - Nov 9
Total with taxes and fees
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
$106 nightly
The price is $120 total per night from Nov 24 to Nov 25
$120 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Our room was very clean the staff was awesome very polite and helpful! We love the pool and hot tub! Will definitely go back!"

Reviewed on Oct 25, 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
$106 nightly
The price is $120 total per night from Nov 26 to Nov 27
$120 total
Nov 26 - Nov 27
Total with taxes and fees
9.2/10 Wonderful! (754 reviews)
"Five stars top to bottom, clean room, easy access, friendly staff very good breakfast exercise room is small but everything you needed for a quick workout."

Reviewed on Oct 27, 2026

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 800 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 $579 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.