Pleasant Prairie Holiday Rentals

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Holiday Rentals in Pleasant Prairie

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, 8 reviews
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is NZ$430
per night
23 Jun - 24 Jun
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, 42 reviews
"Getaway"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
9.8 out of 10, Exceptional, 182 reviews
"Our family had a lot of fun! We stayed four nights and three full days to enjoy all the things the property had to offer. :)"
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
Entire 3 Bedroom Cozy Unit
10.0 out of 10, Exceptional, 3 reviews
"Came for Navy event and had a good night's rest"
The price is NZ$518
per night
24 Jun - 25 Jun
Entire 3 Bedroom Cozy Unit
Unique and Charming Private Quarters
10.0 out of 10, Exceptional, 37 reviews
"Many living indoor and outdoor spaces! Relaxing and peaceful atmosphere. Loved, loved, loved our stay! Thank you Sandy, we'll be back!"
The price is NZ$175
per night
23 Jun - 24 Jun
Unique and Charming Private Quarters
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
7.0 out of 10, Good, 12 reviews
"The check-in process was the easiest part of this stay, and the neighborhood was nice. However, the house needs some upgrades: • The countertop is covered in tape. • There are holes in the walls and noticeable damage from prior use. • Supplies were lacking, with only one towel provided for a family and no paper towels or hand towels available. • The soap dispenser in the shower was mostly empty. • The tub spout was falling off. • There is tape on the baseboards. • The wood floor was...
The price is NZ$400
per night
8 Jul - 9 Jul
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
Lake/Beach Getaway (Remodeled)
10.0 out of 10, Exceptional, 15 reviews
"The view is to die for lots of places walk dogs. The house gave us everything we needed. It is very peaceful. Thank you"
The price is NZ$335
per night
17 Jul - 18 Jul
Lake/Beach Getaway (Remodeled)
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
10.0 out of 10, Exceptional, 32 reviews
"This house has everything you need for a great getaway! It was clean, very well-appointed, and had lots of space to spread out. The beds were comfy, the coffee bar was well stocked, and there was even a station set up with waffle mix, makers, and fixins'. Mike (property owner) responded quickly to our questions and Carrie (property manager) was delightful! There is a reason this place has so many glowing reviews...HIGHLY RECOMMEND!"
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
A Diamond in the Rough
9.4 out of 10, Exceptional, 82 reviews
"Water was high so no beach."
A Diamond in the Rough
Roxan Corner
8.8 out of 10, Excellent, 19 reviews
"This duplex was perfect for my three sons and myself. We stayed five days to attend one of my son’s Navy Graduation! House was very clean and modern. Had everything we needed, was a nice neighborhood, quiet neighbors? Close to everywhere we needed to go. Only suggestion would be to have the owners secure the rugs, they are very slippery. "
Roxan Corner
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, 10 reviews
"My impression of the inside was good. However the outside needs some work. Maybe some up grades in the furniture would be beneficial. Other then that it was an enjoyable experience Thank u"
Fully Updated home. Great for the entire family!
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.4 out of 10, Exceptional, 12 reviews
"Its comfy family house.Near in Naval base,super market and restaurant. Well recommended to stay for graduation or vacation. The owner is fast to communicate. Our overall stay is ❤️.Thank you so much💕💕💕"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
House with great location!
10.0 out of 10, Exceptional, 13 reviews
"Wonderful town. The trail was steps from the front door of this great little cottage. We enjoyed every minute of our visit."
The price is NZ$431
per night
8 Jul - 9 Jul
House with great location!
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, 222 reviews
"The property was beautiful! I just loved watching the sunrise every morning from the master bedroom! The only suggestion I have is to put in writing, in the rules book or a little sign by the refrigerator, how sensitive stainless steel is for those who do not own any stainless steel appliances."
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Pet Friendly Huge Lake Front Home with Stunning Views
9.8 out of 10, Exceptional, 40 reviews
"Our stay was quiet and cozy for our new Navy graduate fresh from bootcamp. It was important to her to have a nice low key stay without a lot of activity surrounding her. We were even able to extend one more day to be able to spend extra time with her."
Pet Friendly Huge Lake Front Home with Stunning Views
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, 47 reviews
"We loved the place and its historic charm!"
The price is NZ$512
per night
9 Jul - 10 Jul
Quaint Bungalow, near Great Lakes Naval Base
Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach
9.8 out of 10, Exceptional, 31 reviews
"House was great. Had everything we could ask for!!"
Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
10.0 out of 10, Exceptional, 64 reviews
"If you rent this property, you will not be disappointed. My wife, daughter, and I highly recommend this VRBO. Its clean and fresh and exactly like it is stated in the advertising. We were also able to rent a pontoon boat as a separate agreement with the owner. The boat was also newer and clean. I don't think that you can find a better place on the chain!"
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
SPACIOUS and Stylish Lakefront Retreat with VIEWS!
9.4 out of 10, Exceptional, 23 reviews
"We booked this home for a long weekend for our book club. Honestly, we are all counting down the days until we have an excuse to do it again! The house is beautiful, well cared for and the hosts were super responsive. The layout is great for multiple couples, offering nice sized bedrooms and multiple full bathrooms. The fire pit on the water was a fan favorite as well, a perfect setting for sunset views. We can’t say enough about our experience and will definitely be returning yearly!"
SPACIOUS and Stylish Lakefront Retreat with VIEWS!
Lovely 4BR Lakeview House w/ Water Access
9.0 out of 10, Wonderful, 6 reviews
"The house was really nice, we enjoyed our stay, enough space for 10-12 people, the only problem we had was the lighting outside of the house we didn’t have any light after sunset, we had to use our phone to us bbq grill."
Lovely 4BR Lakeview House w/ Water Access
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See all available properties in Pleasant Prairie
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.

Other types of properties in Pleasant Prairie you may be interested in

Days Inn by Wyndham Pleasant Prairie Kenosha
2.5 star property
7.4 out of 10, Good, 149 reviews
"Seemed a trifle run down, but not seriously so. Continental breakfast so so. Semi-tractor trailer parking is excellent which was important rhis trip."
The price is NZ$114
per night
30 Jun - 1 Jul
Days Inn by Wyndham Pleasant Prairie Kenosha
Fairfield Inn & Suites Kenosha Pleasant Prairie
2.5 star property
9.2 out of 10, Wonderful, 518 reviews
"Stay was great. "
The price is NZ$164
per night
30 Jun - 1 Jul
Fairfield Inn & Suites Kenosha Pleasant Prairie
Doubletree by Hilton Pleasant Prairie Kenosha
4.0 star property
8.8 out of 10, Excellent, 800 reviews
"We’ve stayed here a number of times. It’s always clean & staff friendly. 2 warm cookies when we checked in, nice! "
The price is NZ$219
per night
30 Jun - 1 Jul
Doubletree by Hilton Pleasant Prairie Kenosha
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pleasant Prairie holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pleasant Prairie. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pleasant Prairie. Seeing all the best attractions is bound to make you fall in love with Pleasant Prairie. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pleasant Prairie short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Pleasant Prairie?

Yes, there are holiday rentals in Pleasant Prairie close to Jelly Belly Center, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Pleasant Prairie has to offer?

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families : This holiday home rental outside of Pleasant Prairie has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Pleasant Prairie?

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

What can I see and do in Pleasant Prairie?

Lake Michigan and Spring Bluff Forest Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jelly Belly Center. In the wider area, you’ll find popular places such as Six Flags Great America and Naval Base Great Lakes.

What are holiday rentals like in Pleasant Prairie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasant Prairie. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.

Recent reviews of Pleasant Prairie properties
Expedia verified reviews