Pleasant Prairie Vacations from $628

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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.
Tru By Hilton Milwaukee Downtown, WI

Tru By Hilton Milwaukee Downtown, WI

2.5 out of 5
Downtown Milwaukee
Price was $1,063, price is now $628 per person
$628
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
8.2/10 Very Good! (1,004 reviews)
wonderful staff, great location. my only complaint was that the floor of our room was dirty, but everything else seemed really clean. there was no coffee pot in the room, but it was available in the lobby.

Reviewed on Aug 18, 2025

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
Price was $1,262, price is now $719 per person
$719
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9.2/10 Wonderful! (134 reviews)
Very cool building, very walkable to the third district area

Reviewed on Aug 4, 2025

Hotel Metro, Autograph Collection

Hotel Metro, Autograph Collection

4 out of 5
Downtown Milwaukee
Price was $1,175, price is now $696 per person
$696
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
8.2/10 Very Good! (1,001 reviews)
The nicest and roomiest room I have been to in an Autograph Collection. Just need to ask for extra bath towels and there is no luggage rack or note pad.

Reviewed on Jul 25, 2025

Residence Inn Milwaukee Downtown by Marriott

Residence Inn Milwaukee Downtown by Marriott

3 out of 5
Westown
Price was $1,060, price is now $629 per person
$629
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9/10 Wonderful! (1,005 reviews)
Property was clean and staff was friendly. Located close to several options for dining and relaxing. Property had washer and dryer facilities that were extremely clean. I would stay again if revisiting the area.

Reviewed on Aug 15, 2025

Courtyard by Marriott Milwaukee Downtown

Courtyard by Marriott Milwaukee Downtown

3 out of 5
Westown
Price was $1,082, price is now $649 per person
$649
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
8.6/10 Excellent! (1,003 reviews)
I would definitely stay at this hotel again. Was in the middle of downtown walking distance for food bars train. Hotel and staff was amazing hotel is clean and comfortable breakfast is amazing

Reviewed on Aug 3, 2025

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Discover the most popular places to visit in Pleasant Prairie

Pleasant Prairie Premium Outlets

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

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
7.2/10 Good! (438 reviews)
"It was just ok. Picked this place because it was close to where we needed to be. Room was clean and breakfast was ok. Would recommend."

Reviewed on Aug 18, 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
$114 nightly
The price is $129 total per night from Sep 7 to Sep 8
$129 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (922 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
$100 nightly
The price is $114 total per night from Sep 14 to Sep 15
$114 total
Sep 14 - Sep 15
Total with taxes and fees
9.2/10 Wonderful! (639 reviews)
"It was good"

Reviewed on Aug 9, 2025

Fairfield Inn & Suites Kenosha Pleasant Prairie
See all 712 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 $628 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.