Pleasant Prairie Vacation Rentals

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Vacation Rentals in Pleasant Prairie

Modern Lakeside Villa
Outdoor spa tub

Modern Lakeside Villa

10.0 out of 10, Exceptional, (21)
"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "
Modern Lakeside Villa
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, (91)
"We throughly enjoyed our stay! The home was beautiful inside and the outside was nice being on the lake. I definitely would recommend this property to others!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Family frndly TwnHm by navy base
Fridge, microwave, oven, stovetop

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (24)
"Great little place to stay near the base. "
Family frndly TwnHm by navy base
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, (212)
"Great place to stay! "
The price is ￥49,923
￥104,792 total
includes taxes & fees
Oct 2 - Oct 3
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
great home in Waukegan for navy graduate families close distance to navy base!!
Fridge, microwave, oven, stovetop

great home in Waukegan for navy graduate families close distance to navy base!!

9.6 out of 10, Exceptional, (29)
"Great place and very convenient to base"
great home in Waukegan for navy graduate families close distance to navy base!!
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

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

10.0 out of 10, Exceptional, (246)
"Beautiful view, wonderful house. Great morings with coffee on balcony!!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
North Chi retreat – Navy, Sauna, Tiki Bar, Games
Fridge, microwave, oven, stovetop

North Chi retreat – Navy, Sauna, Tiki Bar, Games

9.8 out of 10, Exceptional, (8)
The price is ￥22,928
￥69,728 total
includes taxes & fees
Oct 6 - Oct 7
North Chi retreat – Navy, Sauna, Tiki Bar, Games
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Interior

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

9.2 out of 10, Wonderful, (56)
"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!"
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Fridge, microwave, oven, stovetop

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

9.4 out of 10, Exceptional, (14)
"Very happy with this stay. Clean and everything was as described. Bed was comfy. I would definatly recommend and stay again if needed. "
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Roxan Corner
Fridge, microwave, oven, stovetop

Roxan Corner

8.6 out of 10, Excellent, (41)
"We enjoyed our stay! The neighborhood felt safe and we very much loved the space as they made it quite inviting with books and candles. I would have loved more blankets on the beds but overall we had a great stay!"
Roxan Corner
Lake/Beach Getaway (Remodeled)
Children's area

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (41)
"Perfect for what we needed. Right across from the lake, theres a cool little bature walk there as well."
Lake/Beach Getaway (Remodeled)
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV, fireplace

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.0 out of 10, Wonderful, (29)
"This was a great stay. Cute house with all the amenities . The neighborhood was quiet and close to everything. Definitely recommend for any families coming in for Navy graduations, the house is five minutes away from Great Lakes Navy base. "
New Your Home Away From Home! - Near Great Lakes Naval Base!!
This is a VACATION spot with a million dollar view!
Exterior

This is a VACATION spot with a million dollar view!

9.8 out of 10, Exceptional, (16)
"The house was beautiful and very close to my sisters house"
The price is ￥26,626
￥49,537 total
includes taxes & fees
Oct 4 - Oct 5
This is a VACATION spot with a million dollar view!
3-bedroom vacation home just a short walk to Lake Michigan
Terrace/patio

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

9.0 out of 10, Wonderful, (30)
"We stayed for one night since we had a nearby reservation and were coming from Chicago. Location was terrific and we wanted to keep it mind for future booking in the summertime given the proximity to the beach. Really large yard was a plus and accommodations were in nice shape! "
The price is ￥17,972
￥37,524 total
includes taxes & fees
Oct 13 - Oct 14
3-bedroom vacation home just a short walk to Lake Michigan
Beach Lake Michigan King Bed Pet Friendly
On the beach

Beach Lake Michigan King Bed Pet Friendly

9.2 out of 10, Wonderful, (9)
"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
Entire Beautiful Grove Home
Fridge, microwave, oven, stovetop

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
Beautiful and spacious lakefront home! Close to everything!
Exterior detail

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (51)
"A three night stay We were comfortable and pleased with all the amenities. Fishing by the dock, kayaking and enjoying an adult beverage. A magical place to celebrate a new stage. Just one hour away but distant enough to relax the mind "
Beautiful and spacious lakefront home! Close to everything!
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Marina

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

9.4 out of 10, Exceptional, (15)
"Great place to stay! Very nice boat and beautiful area. Host was very prompt in responding and easy to work with. "
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
A Diamond in the Rough
Outdoor dining

A Diamond in the Rough

9.4 out of 10, Exceptional, (92)
"I will be staying here again in the future. Great place at a great location."
A Diamond in the Rough
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, (11)
"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 ￥154,436
￥258,671 total
includes taxes & fees
Oct 6 - Oct 7
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
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

Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

10/10 Excellent
"I love staying here when I go to Waukegan, I love the hotel and the refrigerator and the staff Is great"
Teresa 3-night trip
Posted 12 hours ago
Sonesta ES Suites Chicago Waukegan Gurnee

Find out more about Pleasant Prairie

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?

New Your Home Away From Home! - Near Great Lakes Naval Base!!: This vacation home rental outside of Pleasant Prairie is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings.

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.