A pond surrounded by grass and trees, with a wooden bridge in the background.

Pleasant Prairie Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pleasant Prairie holiday rentals

A house with a front porch, steps, and a small garden area.

1. Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
9.4 out of 10, Exceptional, (96 reviews)
"Comfy, cozy, and clean place to stay!!"
United States
Erin
The price is AU$136
includes taxes & fees
11 Nov - 12 Nov
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A living room with a television on a stand, a potted plant, a glass coffee table, and a window with curtains.

2. Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house
Old Mill Creek
8.6 out of 10, Excellent, (20 reviews)
"The place is very cozy and inviting. There was a smell we thought might have been cat urine on a blanket. Otherwise I'd recommend it."
United States
Matt H.
The price is AU$345
includes taxes & fees
13 Oct - 14 Oct
Apartment Attached to a 1900 historic Farm house
A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

3. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
Salem
The price is AU$1,168
includes taxes & fees
26 Oct - 27 Oct
Salem Vacation Home w/ Dock: Steps to Paddock Lake
A living room with a sofa, coffee table, lamp, and a staircase.

4. Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
9.6 out of 10, Exceptional, (4 reviews)
"Great stay was clean and in a great location overall was a good experience!"
United States
Tristan P.
The price is AU$382
includes taxes & fees
13 Oct - 14 Oct
Cute & Cozy, 1bd Condo Apartment/townhouse
A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

5. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
Salem
9.2 out of 10, Wonderful, (11 reviews)
"Was a nice little get away location. "
United States
Shanna D.
The price is AU$1,155
includes taxes & fees
17 Oct - 18 Oct
Salem Vacation Home w/ Dock: Steps to Paddock Lake
A modern living space with a kitchen, dining area, and a cozy seating area.

6. Charming 2-bedroom Channel house and kayaks in Paddock Lake

Charming 2-bedroom Channel house and kayaks in Paddock Lake
Salem
10.0 out of 10, Exceptional, (13 reviews)
"Excellent property and location!"
United States
Rod L.
The price is AU$364
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom Channel house and kayaks in Paddock Lake
A modern living room with a sofa, a blue armchair, a coffee table, and a TV mounted on the wall.

7. The Beach Park Retreat

The Beach Park Retreat
Beach Park
10.0 out of 10, Exceptional, (1 review)
"The host, Hugo, was friendly and answered questions promptly, the apartment was spacious and well maintained. The kitchen had everything we needed for a weekend trip. I would recommend this property to anyone staying in the area."
United States
Sara
The price is AU$368
includes taxes & fees
20 Oct - 21 Oct
The Beach Park Retreat
A kitchen with wooden cabinets, a black countertop, and a window.

8. Beautiful and Cozy With 5 Bedrooms

Beautiful and Cozy With 5 Bedrooms
Zion
8.8 out of 10, Excellent, (23 reviews)
"This is a great home with plenty of space!"
United States
randy w.
The price is AU$1,058
includes taxes & fees
17 Oct - 18 Oct
Beautiful and Cozy With 5 Bedrooms
An outdoor patio with a hot tub, wicker chairs, and a table.

9. Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is AU$600
includes taxes & fees
13 Oct - 14 Oct
Tiny Home Retreat with hot tub
A glass-enclosed gazebo with a metal roof, wooden deck, and a statue of a person.

10. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is AU$351
includes taxes & fees
21 Oct - 22 Oct
Wisconsin Treehouse Getaway!
A well-lit patio area with a brick wall, a door, a bench, and potted plants.

11. The Rooftop - Haven!

The Rooftop - Haven!
Waukegan
The price is AU$385
includes taxes & fees
18 Oct - 19 Oct
The Rooftop - Haven!
A two-story house with a stone chimney, a front porch with steps, and a flag.

12. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is AU$499
includes taxes & fees
13 Oct - 14 Oct
Quaint Bungalow, near Great Lakes Naval Base
An outdoor patio with a hot tub, wicker chairs, and a table.

13. Hot Tub Retreats

Hot Tub Retreats
Lake Villa
6.0 out of 10, (2 reviews)
"Very disgusting wanted us to throw our poop paper in a waste basket and not flush it down the toilet told me that the previous people that rented took off with the key never changed the locks. Just had to deal with it. Very bad poor communication no information prior to arriving worst place ever."
United States
April R.
The price is AU$472
includes taxes & fees
13 Oct - 14 Oct
Hot Tub Retreats
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

14. 3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Waukegan
9.6 out of 10, Exceptional, (31 reviews)
"Excellent location for Navy Graduation and clean. 5 minutes to the Metra Train. Property owner is very responsive and flexible. Beds were comfortable and double sink in the 1 bathroom was a plus."
United States
Shannon W.
The price is AU$552
includes taxes & fees
1 Nov - 2 Nov
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A kitchen counter with a coffee maker, a water dispenser, a knife block, and a Keurig coffee maker.

15. Greenwood Loft & Rooftop

Greenwood Loft & Rooftop
Waukegan
The price is AU$374
includes taxes & fees
20 Oct - 21 Oct
Greenwood Loft & Rooftop
A spacious living area with a grey sofa, wooden flooring, and a kitchen area with a bar.

16. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (17 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is AU$418
includes taxes & fees
13 Oct - 14 Oct
Richmond No. 267 Boutique Loft Apartment
A living room with a green sofa, a glass coffee table, and a black and white striped rug.

17. 6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags

6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
Waukegan
10.0 out of 10, Exceptional, (1 review)
"Great place for overnight stay. Plenty of room for family of 7. Way better than staying at a hotel."
United States
Kim K.
The price is AU$507
includes taxes & fees
18 Oct - 19 Oct
6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
A house by a lake with docked boats and a flag.

18. This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!
fox lake
9.8 out of 10, Exceptional, (34 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is AU$964
includes taxes & fees
13 Oct - 14 Oct
This is a VACATION spot with a million dollar view!
A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

19. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
The price is AU$932
includes taxes & fees
13 Oct - 14 Oct
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
A beach with a wooden bench, a dock, and calm water.

20. Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva

Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
Burlington
9.2 out of 10, Wonderful, (15 reviews)
"Nice comfy home. Very relaxing"
United States
linda b.
The price is AU$457
includes taxes & fees
4 Nov - 5 Nov
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
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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Top Pleasant Prairie Hotel Reviews

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

8/10 Good
"The property was clean and the staff were friendly. This is a great value"
Misty 2-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

Find out more about Pleasant Prairie

Everything you need to know about Pleasant Prairie holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Prairie holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Prairie holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pleasant Prairie holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Prairie. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasant Prairie holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasant Prairie holiday rentals we have selected for you start as low as AU$345 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pleasant Prairie rentals

At Expedia, we put the best Pleasant Prairie holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pleasant Prairie rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Prairie holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Prairie. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Pleasant Prairie?

Yes, there are holiday rentals where you'll be just 12.8 mi (20.6 km) from Six Flags Great America, providing a secluded option if you want peace and quiet. The shops and restaurants are several reasons why visitors like Pleasant Prairie. Make sure you have time to check out the lake views and temples during your trip.

What are some of the best holiday rentals that Pleasant Prairie has to offer?

Pleasant 3-bedroom house with occupied basement separate entrance.: This holiday home rental outside of Pleasant Prairie has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Pleasant Prairie?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Pleasant Prairie stay.

What can I see and do in Pleasant Prairie?

Lake Michigan and Spring Bluff Forest Preserve are a couple of lovely local spots to get outside and enjoy nature. While here, Pleasant Prairie RecPlex and Pleasant Prairie Premium Outlets are other places worth a visit.

What are holiday rentals like in Pleasant Prairie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasant Prairie. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.