Pleasant Prairie Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Pleasant Prairie

Outdoor spa tub
Modern Lakeside Villa

Modern Lakeside Villa

Pleasant Prairie
10.0 out of 10, Exceptional, (24)
"This is a beautiful home in a even more beautiful location. A perfect place to rest and relax."
United States
Laurie H.
Modern Lakeside Villa
Dining
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Fox Lake
10.0 out of 10, Exceptional, (96)
"Clean with very nice view."
United States
Thomas K.
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Exterior detail
Beautiful and spacious lakefront home! Close to everything!

Beautiful and spacious lakefront home! Close to everything!

Antioch
9.6 out of 10, Exceptional, (56)
"Great place, clean, spacious, as good as advertised! Plenty of things for everyone including the water activities on the lake. Not our first time here or our last. Thanks George!"
United States
Anonymous traveler
Beautiful and spacious lakefront home! Close to everything!
Outdoor pool, a heated pool
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Caledonia
9.8 out of 10, Exceptional, (213)
"Was very impressed with everything, with so many great accommodations this place was so relaxing and fun! Would 10/10 recommend to any one looking for the perfect getaway!"
United States
Ashley H.
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!!

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

Burlington
9.8 out of 10, Exceptional, (93)
"We loved the beach the kids could have stayed there all day! Fishing was wonderful too! Such a fun house!"
United States
Kelly C.
The price is ￥30,910
￥93,102 total
includes taxes & fees
Nov 30 - Dec 1
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

Richmond
9.4 out of 10, Exceptional, (110)
"easy to work with , lots of activities in the area"
United States
JORDAN S.
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Fridge, microwave, oven, stovetop
Family frndly TwnHm by navy base

Family frndly TwnHm by navy base

2.0 star property
Waukegan
9.8 out of 10, Exceptional, (30)
"Enjoyed our stay to visit our recruit for graduation. Naval base was very close. Neighborhood was nice and quiet. Jesse responded promptly to additional request or questions. Would definitely return. "
United States
Marcia W.
Family frndly TwnHm by navy base
Smart TV, fireplace
Rustic Riverside A-Frame Retreat: Secluded Charm.

Rustic Riverside A-Frame Retreat: Secluded Charm.

Racine
9.8 out of 10, Exceptional, (24)
"Loved our stay! Place is super cute and well kept. Had everything you would need. Bed was a little soft for us but works. Cabin is close enough to see everything but far enough away to feel secluded. Loved being right off root river! Great place for kayaking. We caught a wide verity of fish just playing around off 1 lure the entire stay 😂. I would highly recommend this place! We will definitely be back! Thanks again!"
United States
Jamie T.
Rustic Riverside A-Frame Retreat: Secluded Charm.
Microwave, oven, stovetop, dishwasher
Value Stay: Home - 2 Bedrooms

Value Stay: Home - 2 Bedrooms

2.0 star property
Waukegan
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.
The price is ￥15,455
￥37,508 total
includes taxes & fees
Nov 17 - Nov 18
Value Stay: Home - 2 Bedrooms
Fridge, microwave, oven, stovetop
Large Group Retreat w/ secluded party room and private pool

Large Group Retreat w/ secluded party room and private pool

Fox Lake
7.8 out of 10, Good, (22)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
United States
Derek K.
Large Group Retreat w/ secluded party room and private pool
Fridge, microwave, oven, stovetop
Charming 3-bedroom house in Grayslake

Charming 3-bedroom house in Grayslake

Gages Lake
10.0 out of 10, Exceptional, (23)
"We just stayed for the night but it was the perfect place for our family of 5."
United States
James B.
Charming 3-bedroom house in Grayslake
Property grounds
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

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

Kenosha
9.6 out of 10, Exceptional, (87)
"Very clean and quiet. Nice stay. "
United States
Elizabeth D.
The price is ￥10,046
￥17,016 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Outdoor dining
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

Spring Grove
10.0 out of 10, Exceptional, (14)
"Our family loved this property. Perfect space for our family of 15; the pool was the icing on the cake. We appreciated all the amenities , and the extra touch of beautiful fresh flowers did not go unnoticed. Great setup in the kitchen for preparing meals. The kiddos loved the ability to play video games. Great place. "
United States
Diane L.
The price is ￥183,528
￥295,727 total
includes taxes & fees
Nov 17 - Nov 18
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Property grounds
Lakefront home with firepit, 2 kitchens, & 2 W/Ds

Lakefront home with firepit, 2 kitchens, & 2 W/Ds

Antioch
8.8 out of 10, Excellent, (16)
"We had a wonderful long weekend at this property located on the Lake Marie shoreline. The house layout was perfect for the 10 of us! Very clean when we arrived and no issues during our stay!"
United States
Pamela I.
Lakefront home with firepit, 2 kitchens, & 2 W/Ds
Property grounds
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

Bristol
8.6 out of 10, Excellent, (8)
"Home was very clean, cozy and had everything we needed to make our stay the relaxing getaway we hoped for. Lawn could have been mowed before our arrival so we could have enjoyed the beautiful back yard area more."
United States
June
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
Fridge, microwave, oven, stovetop
Fox River/Chain of Lakes Waterfront Home with Hot Tub

Fox River/Chain of Lakes Waterfront Home with Hot Tub

McHenry
10.0 out of 10, Exceptional, (38)
"Great property for a family get together. Very spacious and well equipped. Kristin was excellent!"
United States
Daniel B.
Fox River/Chain of Lakes Waterfront Home with Hot Tub
Exterior
Large Lakehouse with hot tub. walk to public beach in Twin Lakes WI

Large Lakehouse with hot tub. walk to public beach in Twin Lakes WI

Twin Lakes
9.8 out of 10, Exceptional, (14)
"Decor is quite interesting. Driveway is very narrow. Luxury upstairs shower was broken during our stay."
United States
Lauren W.
Large Lakehouse with hot tub. walk to public beach in Twin Lakes WI
Interior
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

Twin Lakes
9.2 out of 10, Wonderful, (57)
"Great people to work with!"
United States
Nicholas H.
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Property grounds
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Kenosha
10.0 out of 10, Exceptional, (248)
"Lots of space, beautiful view Loved our stay."
United States
Karen C.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds
Spacious 27’ RV on horse farm

Spacious 27’ RV on horse farm

Bristol
8.6 out of 10, Excellent, (8)
"Beautiful property and very nice and friendly people "
United States
Jeff K.
Spacious 27’ RV on horse farm
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

La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

10/10 Excellent
"All good."
Sally 2-night trip
Posted 12 hours ago
La Quinta Inn & Suites by Wyndham Chicago Gurnee

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:

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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?

Beautiful and spacious lakefront home! Close to everything!: This vacation home rental outside of Pleasant Prairie is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Pleasant Prairie?

With 5 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. In the larger area, you’ll find popular places like Naval Base Great Lakes and Six Flags Great America.

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.