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

Pleasant Prairie Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Pleasant Prairie holiday rentals

Interior

1. 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 HK$1,898
HK$7,055 total
includes taxes & fees
23 Sept - 24 Sept
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Smart TV

2. 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 HK$861
HK$1,985 total
includes taxes & fees
21 Sept - 22 Sept
Cute & Cozy, 1bd Condo Apartment/townhouse
TV

3. 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 HK$1,506
HK$7,217 total
includes taxes & fees
23 Sept - 24 Sept
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Exterior

4. 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 HK$855
HK$1,987 total
includes taxes & fees
22 Sept - 23 Sept
The Beach Park Retreat
Interior

5. 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 HK$3,138
HK$5,936 total
includes taxes & fees
21 Sept - 22 Sept
Beautiful and Cozy With 5 Bedrooms
Smart TV

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 HK$1,177
HK$1,978 total
includes taxes & fees
1 Oct - 2 Oct
Charming 2-bedroom Channel house and kayaks in Paddock Lake
TV, books, stereo

7. The Rooftop - Haven!

The Rooftop - Haven!
Waukegan
The price is HK$855
HK$2,124 total
includes taxes & fees
21 Sept - 22 Sept
The Rooftop - Haven!
Interior

8. 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 HK$988
HK$1,904 total
includes taxes & fees
27 Sept - 28 Sept
Apartment Attached to a 1900 historic Farm house
TV

9. Greenwood Loft & Rooftop

Greenwood Loft & Rooftop
Waukegan
The price is HK$777
HK$1,924 total
includes taxes & fees
26 Sept - 27 Sept
Greenwood Loft & Rooftop
Outdoor pool, a heated pool

10. Marina Life II - 28 Carver @ Reef Point Marina

Marina Life II - 28 Carver @ Reef Point Marina
Racine
9.8 out of 10, Exceptional, (57 reviews)
"Very beautiful unique experience. Wonderful clean facilities, would definitely stay again"
United States
Paul
The price is HK$1,177
HK$1,895 total
includes taxes & fees
21 Sept - 22 Sept
Marina Life II - 28 Carver @ Reef Point Marina
Exterior

11. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is HK$988
HK$1,950 total
includes taxes & fees
21 Sept - 22 Sept
Wisconsin Treehouse Getaway!
Outdoor dining

12. Hot Tub Retreats

Hot Tub Retreats
Lake Villa
10.0 out of 10, Exceptional, (1 review)
"Very clean and cozy I loved my stay"
United States
Rosilynn B.
The price is HK$1,875
HK$2,627 total
includes taxes & fees
22 Sept - 23 Sept
Hot Tub Retreats
Interior

13. Irish Mist V @ Reefpoint Marina

Irish Mist V @ Reefpoint Marina
Racine
9.8 out of 10, Exceptional, (40 reviews)
"Nice spot to stay a night!"
United States
Joseph P.
The price is HK$1,059
HK$1,986 total
includes taxes & fees
21 Sept - 22 Sept
Irish Mist V @ Reefpoint Marina
Outdoor dining

14. 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 HK$1,796
HK$3,317 total
includes taxes & fees
27 Sept - 28 Sept
Tiny Home Retreat with hot tub
3 bedrooms, desk, iron/ironing board, travel cot

15. 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, (27 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 HK$1,255
HK$3,081 total
includes taxes & fees
21 Sept - 22 Sept
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Beach nearby

16. 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, (14 reviews)
"Nice comfy home. Very relaxing"
United States
linda b.
The price is HK$1,200
HK$2,384 total
includes taxes & fees
28 Sept - 29 Sept
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
Living area

17. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (16 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is HK$1,353
HK$2,284 total
includes taxes & fees
24 Sept - 25 Sept
Richmond No. 267 Boutique Loft Apartment
Exterior detail

18. 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 HK$1,059
HK$2,793 total
includes taxes & fees
21 Sept - 22 Sept
Quaint Bungalow, near Great Lakes Naval Base
Smart TV

19. 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
The price is HK$1,059
HK$2,769 total
includes taxes & fees
22 Sept - 23 Sept
6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
Smart TV, fireplace, table football, video library

20. Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Gurnee
9.4 out of 10, Exceptional, (43 reviews)
"Great space for the kids and adults.The pool table was very popular. Located close to the Great Lakes Naval Station so it was convenient to pickup/drop off our Sailor during liberty. Host was very accommodating and great in making sure we had a good experience."
United States
Jim L.
The price is HK$3,491
HK$5,645 total
includes taxes & fees
13 Oct - 14 Oct
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasant Prairie Hotel Reviews

Red Roof Inn Gurnee - Waukegan

Red Roof Inn Gurnee - Waukegan

10/10 Excellent
"honestly our first time there and they did not disappoint , i just wish they did have like a few snacks just incase but overall everything else was good , the beds were comfortable and the area was not bad"
ashley 4-night trip
Posted 19 hours ago
Red Roof Inn Gurnee - Waukegan

Find out more about Pleasant Prairie

Search for holiday rentals in Pleasant Prairie on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasant Prairie using one of the methods below:

  • View our selection of featured holiday rentals in Pleasant Prairie
  • Use the map to find apartments and other holiday homes in the Pleasant Prairie neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pleasant Prairie while they last

Look no further and take a look at our great range of rental properties in Pleasant Prairie!

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?

Stylish Great Lakes Getaway • 4 Min to Navy Base • Family-Friendly 2BR: This holiday home rental outside of Pleasant Prairie offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of games in this rental home to help you unwind.

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.