
Pleasant Prairie Vacations from $425
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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.

County Clare Irish Hotel & Pub
Downtown Milwaukee
Price was $545, price is now $425 per person
$425
per person
Sep 10 - Sep 13
found 18 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.6/10 Exceptional! (1,003 reviews)
Average space in rooms no port plugins, must bring your own. Older furniture and bed.
Parking can be difficult. Breakfast does not start until 8 am.
Reviewed on Jun 14, 2026

Saint Kate - The Arts Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $1,358, price is now $827 per person
$827
per person
Sep 3 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.8/10 Exceptional! (2,632 reviews)
Beautiful room. The entry is dominated by a central bar. On night we stayed the bar was crowded and noisy. Did not bother room silenced but was jarring when entering hotspot and no way to get a seat or drink at bar. Great art but felt like NYC on Friday date nights.
Reviewed on Jun 14, 2026

The Pfister Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $1,528, price is now $959 per person
$959
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9.6/10 Exceptional! (2,119 reviews)
Can't imagine there is a better place to stay in Milwaukee. Excellent location. Beautiful hotel. The lobby is great. Room very well maintained. People who work there are very helpful and knowledgeable.
Reviewed on Jun 16, 2026

Kinn Guesthouse Bay View
Bay View
Price was $721, price is now $528 per person
$528
per person
Sep 10 - Sep 13
found 18 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.4/10 Exceptional! (466 reviews)
Great location! Walking distance to some great bars, food and shopping. Some minor fixes to both the room and common area needed.
Reviewed on Jun 14, 2026

Dubbel Dutch
Downtown Milwaukee
Price was $739, price is now $584 per person
$584
per person
Sep 3 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.2/10 Wonderful! (148 reviews)
There is a bar in the building that is loud until midnight. The parking fee was higher than the site warranted. The sofa couch was not suitable for any over 5' tall. It all depends on the room you get in terms of the experience. I would not stay there again, as it was more costly and had little to recommend it. No microwave in the room. Fridge froze my food overnight, making it useless and uneatable. NOT appropriate if you cannot walk up steps easily. I think a regular hotel room would have offered better service at a more reasonable price.
Reviewed on Oct 28, 2025
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Pleasant Prairie Hotel Deals

Days Inn by Wyndham Pleasant Prairie Kenosha
7540 118th Ave Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $88 total per night from Jun 21 to Jun 22
$88 total
Jun 21 - Jun 22
Total with taxes and fees
8.2/10 Very Good! (469 reviews)
"The hotel was ok. Most of the doors were propped open from hotel guests and the whole stairwell smelled like cigarettes. The room was ok. Floor had some bubble ups on certain spots and the toilet moved when you used it like it was loose from the ground. Overall it was ok for the price."
Reviewed on Jun 15, 2026

Doubletree by Hilton Pleasant Prairie Kenosha
11800 108th St Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $128 total per night from Jul 5 to Jul 6
$128 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (994 reviews)
"*"
Reviewed on Jun 9, 2026

Fairfield Inn & Suites Kenosha Pleasant Prairie
10601 120TH AVENUE Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Jul 5 to Jul 6
$124 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (721 reviews)
"Our room was very clean, staff is excellent; always helpful. The breakfast has many options to choose from, well supplied & perfectly clean. Parking couldn’t be better!"
Reviewed on Jun 7, 2026
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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