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

Holiday Homes in Pleasant Prairie

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Pleasant Prairie holiday homes

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$140
includes taxes & fees
21 Nov - 22 Nov
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A modern living space with a kitchen, dining area, and a cozy seating area.

2. 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$361
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom Channel house and kayaks in Paddock Lake
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
Salem
9.2 out of 10, Wonderful, (12 reviews)
"Was a nice little get away location. "
United States
Shanna D.
The price is AU$1,168
includes taxes & fees
13 Nov - 14 Nov
Salem Vacation Home w/ Dock: Steps to Paddock Lake
A kitchen with wooden cabinets, a black countertop, and a window.

4. 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$1,042
includes taxes & fees
26 Oct - 27 Oct
Beautiful and Cozy With 5 Bedrooms
A modern living room with a sofa, a TV, and a kitchen area with a fridge and bar stools.

5. Peaceful and Cozy Place to Stay

Peaceful and Cozy Place to Stay
Waukegan
The price is AU$407
includes taxes & fees
2 Nov - 3 Nov
Peaceful and Cozy Place to Stay
A two-story house with a stone chimney, a front porch with steps, and a flag.

6. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (76 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is AU$496
includes taxes & fees
31 Oct - 1 Nov
Quaint Bungalow, near Great Lakes Naval Base
An outdoor patio with a hot tub, wicker chairs, and a table.

7. 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$464
includes taxes & fees
5 Nov - 6 Nov
Hot Tub Retreats
A snow-covered outdoor area with a central fire pit surrounded by wooden stools, string lights overhead, and a building in the background.

8. 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
9.8 out of 10, Exceptional, (15 reviews)
"Nice comfy home. Very relaxing"
United States
linda b.
The price is AU$488
includes taxes & fees
4 Nov - 5 Nov
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
A two-story house with a balcony, a flag, and outdoor seating.

9. 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$959
includes taxes & fees
28 Oct - 29 Oct
This is a VACATION spot with a million dollar view!
A living room with a green sofa, a glass coffee table, and a black and white striped rug.

10. 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, (2 reviews)
"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$501
includes taxes & fees
25 Oct - 26 Oct
6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
Interior

11. Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
North Chicago
7.6 out of 10, Good, (7 reviews)
"We enjoyed our stay, just had a few issues with air conditioning, but host was able to get it fixed quickly."
United States
Gregory S.
The price is AU$726
includes taxes & fees
26 Oct - 27 Oct
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
A modern living room with dark hardwood floors, white sofas, a round mirror, and a dining area with a table and chairs.

12. Great America Getaway | Sleeps 12 | Near Navy Base

Great America Getaway | Sleeps 12 | Near Navy Base
Gurnee
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Loved property"
United States
Jennifer R.
The price is AU$1,032
includes taxes & fees
25 Oct - 26 Oct
Great America Getaway | Sleeps 12 | Near Navy Base
A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

13. 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$861
includes taxes & fees
26 Oct - 27 Oct
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
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

Best Western Executive Inn Kenosha/Pleasant Prairie

Best Western Executive Inn Kenosha/Pleasant Prairie

10/10 Excellent
"Helpful staff with a good choice of food at Breakfast."
David 1-night trip
Posted 6 hours ago
Best Western Executive Inn Kenosha/Pleasant Prairie

Find out more about Pleasant Prairie

Pleasant Prairie Holiday Homes information

Number of reviews
243
Accommodation
338 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$1,168