Pleasant Prairie Vacation Rentals

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Check prices for these dates

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Aug 14 - Aug 15
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Aug 15 - Aug 16
This weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Pleasant Prairie

Modern Lakeside Villa
Outdoor spa tub

Modern Lakeside Villa

10.0 out of 10, Exceptional, (19)
"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "
Modern Lakeside Villa
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar
Property grounds

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

10.0 out of 10, Exceptional, (3)
"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar
Tiny Home Retreat with hot tub
Outdoor dining

Tiny Home Retreat with hot tub

8.0 out of 10, Very Good, (2)
"We had the most wonderful time"
The price is ￥18,995
￥44,787 total
includes taxes & fees
Aug 17 - Aug 18
Tiny Home Retreat with hot tub
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
Property grounds

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

10.0 out of 10, Exceptional, (2)
"We were there for a horse show and it was the perfect place after a long day at the show. "
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (14)
"The house, yard and location were all perfect. "
The price is ￥39,021
￥73,190 total
includes taxes & fees
Sep 1 - Sep 2
Charming 3-bedroom house in Grayslake
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, music library, video library, stereo

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Outdoor dining

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

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."
The price is ￥161,828
￥264,670 total
includes taxes & fees
Aug 18 - Aug 19
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Terrace/patio

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

9.4 out of 10, Exceptional, (105)
"We had a great stay at the lakehouse! The property was super nice—clean, cozy, and exactly as described. The owner was very communicative and made the entire process smooth. Overall, it was a really good experience. "
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

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

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Outdoor pool, a heated pool

7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

9.8 out of 10, Exceptional, (209)
"Great place to stay! "
The price is ￥73,625
￥133,135 total
includes taxes & fees
Sep 1 - Sep 2
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Marina Life II - 28 Carver @ Reef Point Marina
Property grounds

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (44)
"This is a super fun place to stay! The marina has excellent amenities and the boat was clean and well appointed."
The price is ￥22,088
￥35,576 total
includes taxes & fees
Aug 15 - Aug 16
Marina Life II - 28 Carver @ Reef Point Marina
The Randolph Hotel Apt 201
Marina

The Randolph Hotel Apt 201

6.0 out of 10, (2)
"Staying in the Round Lake Beach area to visiting family. Room is great and clean. Pretty view of Fox Lake. Only draw back is it is over a bar. Karaoke comes right up through the floor. Not to much of a problem as the bar closes at 11:00. So just have to suffer through the drunken super star want a be singers. It is good for some laughs. Over all I would recommend this place in a heartbeat. "
The price is ￥16,566
￥50,800 total
includes taxes & fees
Aug 25 - Aug 26
The Randolph Hotel Apt 201
Large Group Retreat w/ secluded party room and private pool
Fridge, microwave, oven, stovetop

Large Group Retreat w/ secluded party room and private pool

8.4 out of 10, Very Good, (19)
"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."
Large Group Retreat w/ secluded party room and private pool
Rustic Riverside A-Frame Retreat: Secluded Charm.
Smart TV, fireplace

Rustic Riverside A-Frame Retreat: Secluded Charm.

10.0 out of 10, Exceptional, (15)
"Happy Place, immaculate, well designed, nice mattress, fun easy place with friends"
Rustic Riverside A-Frame Retreat: Secluded Charm.
Cozy RV in our land with community private beach, fire pit, bring your boat.
Property grounds

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.
Beach Lake Michigan King Bed Pet Friendly
On the beach

Beach Lake Michigan King Bed Pet Friendly

9.0 out of 10, Wonderful, (7)
"Judy's townhouse was a perfect spot for us to visit our family in Kenosha. We were all able to gather here to visit and enjoy the beautiful lakefront setting! "
Beach Lake Michigan King Bed Pet Friendly
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

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

9.8 out of 10, Exceptional, (88)
"One of my favorite places I've stayed at "
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Entire Beautiful Grove Home
Smart TV, fireplace

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (11)
"The space of the house was great. Didnt use any of the big back yard. Had a lot of loud music the last two nights. Kept us awake . Even heard with earplugs."
Entire Beautiful Grove Home
3-bedroom vacation home just a short walk to Lake Michigan
Terrace/patio

3-bedroom vacation home just a short walk to Lake Michigan

9.4 out of 10, Exceptional, (27)
"Great location close to the water cute house clean comfortable. Host was very accommodating to my allergy. Needs really enjoyed our stay highly recommend."
The price is ￥19,879
￥40,111 total
includes taxes & fees
Aug 25 - Aug 26
3-bedroom vacation home just a short walk to Lake Michigan
Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table
Terrace/patio

Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table

10.0 out of 10, Exceptional, (4)
"We stayed for two nights and absolutely loved it! The space was cozy and welcoming, and my family felt right at home. The second-floor patio was stunning—we spent both days out there just soaking it all in. The kitchen was beautiful and had everything we needed. Overall, such a wonderful experience and we’d love to come back!"
Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table
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

Comfort Suites Grayslake near Libertyville North

Comfort Suites Grayslake near Libertyville North

10/10 Excellent
"Great place to stay !"
anthony 2-night trip
Posted 21 hours ago
Comfort Suites Grayslake near Libertyville North

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?

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar: This vacation home rental outside of Pleasant Prairie offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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.