Pleasant Prairie Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Pleasant Prairie vacation rentals

Microwave, oven, stovetop, dishwasher
Home -2 bedroom, 4k projector

Vacation Home in Waukegan

Home -2 bedroom, 4k projector
2.0 star property
10.0 out of 10, Exceptional, (2)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
$226 nightly
The price is $240
Dec 13 - Dec 14
Total with taxes and fees
Home -2 bedroom, 4k projector
Property grounds
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Vacation Home in Kenosha

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, (249)
"Great weekend, thank you for the space!"
United States
Ed C.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Outdoor pool, a heated pool
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Vacation Home in Caledonia

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
9.8 out of 10, Exceptional, (213)
"I want to move in. We had 13 guys for a bachelor retreat and this place was perfect. Plenty of room for us all and plenty to do. We expected to spend plenty of time exploring Milwaukee, but found ourselves hanging out at the pool or fishing in the pond when we weren’t relaxing in the game room. 10/10 would recommend!"
United States
Caleb B.
$615 nightly
The price is $648
Dec 21 - Dec 22
Total with taxes and fees
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
Terrace/patio
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

Vacation Home in Burlington

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
9.8 out of 10, Exceptional, (94)
"Hosts went above and beyond to accommodate my senior mother with a private bed on main level. They were also accommodating on other requests that I had. It was such a fun, nostalgic place. It was all exactly how I remembered the Old Mill to be and the private beach made for some additional family time. I see a wonderful future for this getaway place!! "
United States
Tina V.
$857 nightly
The price is $904
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Dining
Island view cottage on crystal clear spring fed lake.

Vacation Home in Burlington

Island view cottage on crystal clear spring fed lake.
10.0 out of 10, Exceptional, (146)
"This home on Brown’s Lake checks every box. It is spacious with plenty of space for 12 of us (9 adults and 3 kids) to spread out. The newly remodeled kitchen is amazing (nicer than mine at home) and has every dish, pot, pan or utensil you could ever need. A screened-in 3 season room is off the kitchen with wonderful views of the lake. There are two master bedrooms, but all of the bedrooms are spacious and are located near bathrooms that are lovely. Everyone in our group had their own space...
United States
Linda C.
Island view cottage on crystal clear spring fed lake.
Terrace/patio
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

Vacation Home in Richmond

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
9.4 out of 10, Exceptional, (110)
"Perfect for hosting a big family party and great space for a getaway! The host helped us with a boat rental and the house was well-stocked with towels and kitchen/bathroom essentials as well as water toys to use on the lake! We had a blast! "
United States
Ashley F.
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Fridge, microwave, oven, stovetop
North Chi retreatNavySaunaTiki BarGames

Vacation Home in North Chicago

North Chi retreatNavySaunaTiki BarGames
10.0 out of 10, Exceptional, (13)
"love the air hocky what a fun way to spend time with the kids! and after a long drive the sauna was a blessing. Also the fire pit and swings was the best way to end our day and spend time together."
United States
Chad H.
$507 nightly
The price is $520
Dec 15 - Dec 16
Total with taxes and fees
North Chi retreatNavySaunaTiki BarGames
Fridge, microwave, oven, stovetop
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

Vacation Home in Gurnee

Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
9.8 out of 10, Exceptional, (23)
"It was perfect for our family. We all had beds to sleep in, they were comfortable and it was just minutes away from Great America. "
United States
Sherri K.
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Outdoor dining
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

Vacation Home in Spring Grove

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
10.0 out of 10, Exceptional, (15)
"Large house, indoor pool, plenty of space for families"
United States
Taylor S.
$1,867 nightly
The price is $1,979
Dec 11 - Dec 12
Total with taxes and fees
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Exterior
Wisconsin Treehouse Getaway!

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (26)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
$216 nightly
The price is $245
Dec 11 - Dec 12
Total with taxes and fees
Wisconsin Treehouse Getaway!
Property grounds
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

Cottage in Bristol

New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
8.6 out of 10, Excellent, (8)
"We were there for a horse show and it was the perfect place after a long day at the show. "
United States
Melissa K.
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
Dining tables
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Vacation Home in North Chicago

New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.0 out of 10, Wonderful, (34)
"Very clean home in a quiet neighborhood "
United States
Angela D.
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Exterior
This is a VACATION spot with a million dollar view!

Vacation Home in fox lake

This is a VACATION spot with a million dollar view!
9.8 out of 10, Exceptional, (19)
"So easy to get to, right in the water. Has a dock for your boat. Sonja is very welcoming. "
United States
Kristina H.
$240 nightly
The price is $254
Dec 14 - Dec 15
Total with taxes and fees
This is a VACATION spot with a million dollar view!
Fridge, microwave, oven, stovetop
3 Mins Wilmot Ski Resort| Year-Round Indoor Heated Pool|Family Reunions|Pickelball/Tennis|Twin Pines

Vacation Home in Twin Lakes

3 Mins Wilmot Ski Resort| Year-Round Indoor Heated Pool|Family Reunions|Pickelball/Tennis|Twin Pines
2.0 star property
3 Mins Wilmot Ski Resort| Year-Round Indoor Heated Pool|Family Reunions|Pickelball/Tennis|Twin Pines
Fridge, microwave, oven, stovetop
Large Group Retreat w/ secluded party room and private pool

Vacation Home in Fox Lake

Large Group Retreat w/ secluded party room and private pool
7.8 out of 10, Good, (22)
"Place is in a state of disarray and should not be rented until repairs are made. Air conditioning is not functioning in the party room, heat on hot tub does not work, most chairs around the pool are broken, we had to buy toilet paper and paper towels, pots and pans in cabinets had not been washed and lights all over the house were out to include overhead lights in the kitchen. "
United States
Jack R.
Large Group Retreat w/ secluded party room and private pool
Interior
Barn! B-Ball Court/Mini Golf/Sports Bar/Tiki Bar/Theater/Arcade/Hot Tub/Fire Pit

Vacation Home in Mount Pleasant

Barn! B-Ball Court/Mini Golf/Sports Bar/Tiki Bar/Theater/Arcade/Hot Tub/Fire Pit
9.8 out of 10, Exceptional, (17)
"this place was absolutely perfect for our group of guys for my bachelor party. so many things to do at the property that we barely left!the space is also great both indoors and outdoorswe will be back!!thanks!"
United States
Leonard M.
Barn! B-Ball Court/Mini Golf/Sports Bar/Tiki Bar/Theater/Arcade/Hot Tub/Fire Pit
Property grounds
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Vacation Home in Kenosha

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
9.6 out of 10, Exceptional, (87)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
$97 nightly
The price is $110
Dec 11 - Dec 12
Total with taxes and fees
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Dining
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

Vacation Home in Twin Lakes

#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
10.0 out of 10, Exceptional, (42)
"Wonderful place and wonderful host!!!"
United States
Catherine C.
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Interior
Welcome To My Loft!

Apartment in Racine

Welcome To My Loft!
10.0 out of 10, Exceptional, (16)
"Great place to stay!"
United States
kathleen
$105 nightly
The price is $111
Dec 14 - Dec 15
Total with taxes and fees
Welcome To My Loft!
Interior
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

Vacation Home in Twin Lakes

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
9.2 out of 10, Wonderful, (57)
"We had a great time! Jeff was easy to communicate with and accommodating to our group. While the property is beautiful, folks should know you cannot swim at the dock. We did rent a pontoon which provided lots of swimming opportunity and fun! Thanks again for a great stay!"
United States
Kelsey H.
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
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

DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

10/10 Excellent
"I checked in I slept the bed was comfy."
Mark 1-night trip
Posted 2 days ago
DoubleTree by Hilton Libertyville - Mundelein

Find out more about Pleasant Prairie

Everything you need to know about Pleasant Prairie vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Prairie vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Prairie vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pleasant Prairie in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasant Prairie rentals

At Expedia, we put the best Pleasant Prairie vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Pleasant Prairie?

Yes, we give you a choice of vacation rentals in Pleasant Prairie close to Jelly Belly Center, or you can select a more remote option if you want a relaxing stay. 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's the top vacation rental that Pleasant Prairie has to offer?

Home -2 bedroom, 4k projector: This vacation 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 vacation rentals are there in Pleasant Prairie?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Pleasant Prairie stay.

What can I see and do in Pleasant Prairie?

Lake Michigan and North Point Marina Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jelly Belly Center. While here, Pleasant Prairie RecPlex and Pleasant Prairie Premium Outlets are other places worth a visit.

What are vacation rentals like in Pleasant Prairie?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Pleasant Prairie. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.