Pleasant Prairie Vacations from $582

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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.
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $719, price is now $582 per person
$582
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)
It was great and a good location. Room was nice.

Reviewed on Nov 1, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $846, price is now $676 per person
$676
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
A beautiful hotel with amazing artwork and a great history.

Reviewed on Nov 2, 2026

The Delafield Hotel

The Delafield Hotel

4 out of 5
Price was $1,043, price is now $853 per person
$853
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Milwaukee (MKE)
9.6/10 Exceptional! (506 reviews)
Q

Reviewed on Nov 1, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $1,029, price is now $851 per person
$851
per person
Dec 22 - Dec 28
found 14 hours ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
9.4/10 Exceptional! (508 reviews)
fantastic and responsive staff. great neighborhood and location. proximity to the lake, restaurants, shops, and downtown. clean modern room. would stay again!

Reviewed on Oct 31, 2026

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Avenues West
Price was $721, price is now $607 per person
$607
per person
Dec 22 - Dec 28
found 14 hours ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
9/10 Wonderful! (1,417 reviews)

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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.
See properties

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
$110 nightly
The price is $125 total per night from Dec 3 to Dec 4
$125 total
Dec 3 - Dec 4
Total with taxes and fees
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
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Nov 22 to Nov 23
$120 total
Nov 22 - Nov 23
Total with taxes and fees
Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 798 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 $582 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.