Pleasant Prairie holiday rentals

We found 183 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Pleasant Prairie that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Pleasant Prairie

Showing deals for:25 Dec - 1 Jan

Living area
Terrace/patio
Living area
Property grounds
Wonderful
(7 reviews)

The Lodge, Sweet Waterfront Cottage, Separate Unit

Antioch

8% off
AU$11,262
for 7 nights, 1 cottage
AU$1,609 per night
includes taxes & fees
The Lodge, Sweet Waterfront Cottage, Separate Unit
Exterior
Interior
Dining
Outdoor dining
Exceptional
(18 reviews)

Windjammer, Lakefront Home-Away-From-Home!!!

Antioch

8% off
AU$12,245
for 7 nights, 1 home
AU$1,749 per night
includes taxes & fees
Windjammer, Lakefront Home-Away-From-Home!!!
Living area
Private kitchen
Dining
Living area
Exceptional
(44 reviews)

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

Waukegan

8% off
AU$3,178
for 7 nights, 1 home
AU$454 per night
includes taxes & fees
great home in Waukegan for navy graduate families close distance to navy base!!
Private kitchen
Dining
Interior
Private kitchen
Exceptional
(26 reviews)

Lake House ON the Water! Hot tub! Kayaks! Boat & Golf Cart Rental! Ski Lessons!

Salem

8% off
AU$5,100
for 7 nights, 1 home
AU$729 per night
includes taxes & fees
Lake House ON the Water! Hot tub! Kayaks! Boat & Golf Cart Rental! Ski Lessons!
Exterior
Property grounds
Interior
Children’s area
Exceptional
(45 reviews)

Cozy Cottage by the Lake! Kayaks! BIG Deck w/ Great Lake Views! Golf Cart Rental

Salem

12% off
AU$2,370
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
Cozy Cottage by the Lake! Kayaks! BIG Deck w/ Great Lake Views! Golf Cart Rental
Living area
Exterior
Property grounds
Dining
Exceptional
(20 reviews)

2BR Lake House - Stunning Views - Lake Toys - Screen Room - K Bed - Dog Friendly

Trevor

8% off
AU$3,014
for 7 nights, 1 home
AU$431 per night
includes taxes & fees
2BR Lake House - Stunning Views - Lake Toys - Screen Room - K Bed - Dog Friendly
Private kitchen
Living room
Available parking on premises for up to 2 vehicles.
Bedroom 1
Exceptional
(42 reviews)

Entire 3 Bedroom Cozy Unit

Waukegan

8% off
AU$2,234
for 7 nights, 1 home
AU$319 per night
includes taxes & fees
Entire 3 Bedroom Cozy Unit

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lakeside setting of Pleasant Prairie is ready to explore

Enjoy the temples and other features of Pleasant Prairie. This city's shopping, restaurants and lake draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Pleasant Prairie

Are you hoping to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Pleasant Prairie a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Six Flags Great America (12.8 mi / 20.6 km)
  • Apple Holler (8.5 mi / 13.7 km)
  • Great Wolf Lodge Water Park (11.7 mi / 18.9 km)
  • Racine Zoological Gardens (15.6 mi / 25.1 km)
  • Greenshire Golf Course (9.8 mi / 15.7 km)
  • Launch Family Entertainment (12.6 mi / 20.2 km)

Exploring the natural features in Pleasant Prairie

Whether you're an active traveller or just want to take in the scenery, Pleasant Prairie is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Simmons Island Beach (6.7 mi / 10.7 km)
  • Waukegan SportsPark (9.5 mi / 15.3 km)
  • Silver Lake Beach (10.8 mi / 17.3 km)
  • Wilmot Mountain (13.8 mi / 22.2 km)
  • Franksville Park (14.1 mi / 22.7 km)
  • Waukegan Harbor (14.3 mi / 23 km)

Transport to and around Pleasant Prairie

The nearest airport is in Kenosha, WI (ENW-Kenosha Regional), located 2.9 mi (4.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Milwaukee, WI (MKE-General Mitchell Intl.), which is 27.4 mi (44 km) away.

Frequently asked questions

What is the best area to stay in Pleasant Prairie when booking a holiday rental?
When considering a holiday rental in Pleasant Prairie, Wisconsin, a popular area to stay is near the picturesque Lake Andrea. This neighbourhood not only offers scenic views but also provides access to a range of outdoor activities. Lake Andrea Park is a fantastic attraction, featuring walking trails, picnic areas, and opportunities for fishing and kayaking, making it great for families and nature enthusiasts alike.Another appealing area is close to the Pleasant Prairie Premium Outlets, which is a popular shopping destination. Here, you can find a variety of brand-name stores, making it an excellent spot for those looking to indulge in a bit of retail therapy. The blend of leisure and shopping in this area ensures that visitors have plenty to enjoy during their stay.While the exact number of properties may vary, Pleasant Prairie has a good selection of holiday rentals that cater to different preferences and budgets, allowing visitors to find accommodations that suit their needs perfectly.
What is the most popular type of holiday rental accomodation in Pleasant Prairie?
In Pleasant Prairie, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically feature spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many homes also include outdoor spaces such as patios or gardens, great for relaxing after a day of exploring the local attractions.
Are there any family house rentals in Pleasant Prairie?
In Pleasant Prairie, Wisconsin, there are several family-friendly house rentals available. This charming area boasts a variety of homes ideal for families looking to enjoy a comfortable stay. Many properties come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces such as patios or gardens where children can play safely.Visitors will appreciate the close proximity to attractions like the Pleasant Prairie Premium Outlets, superb for a day of shopping, as well as nearby parks that offer recreational facilities and picnic areas. The locale also provides easy access to Lake Michigan, where families can enjoy beach activities during warmer months.
Are there pet-friendly house rentals in Pleasant Prairie?
In Pleasant Prairie, there are several pet-friendly house rentals available, making it an excellent choice for travellers with furry companions. Many of these properties come equipped with essential amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The area is conveniently located near parks, providing ample opportunities for pet owners to take their dogs for walks or enjoy a relaxing day outdoors. For instance, the nearby Prairie Springs Park features walking trails and open green spaces, great for both pets and their owners to explore.
Are there any remote work holiday rentals in Pleasant Prairie?
In Pleasant Prairie, Wisconsin, there are several holiday rentals suitable for remote work. Many of these properties are equipped with essential amenities such as free Wi-Fi and dedicated workspaces, allowing guests to comfortably manage their professional tasks while enjoying their stay. The area itself offers a pleasant environment, with nearby attractions such as the scenic Lake Michigan shoreline and the sprawling parks that are superb for breaks or relaxation after a day of work. Additionally, the proximity to local shops and dining options adds convenience for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pleasant Prairie?
In Pleasant Prairie, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature decks or patios, providing outdoor space to relax and enjoy the fresh air. Fireplaces are common, adding a cosy touch for those cooler evenings. Onsite parking is typically available, making it convenient for travellers with vehicles. Additionally, air conditioning is a sought-after amenity, ensuring comfort during the warmer months.
When is the best time to visit Pleasant Prairie for a holiday rental?
The best time to visit Pleasant Prairie for a holiday rental is during the peak season, which runs from May to July. This period attracts travellers, drawn by the warm weather and a wealth of outdoor activities. July, in particular, is the most popular month, offering a lively community atmosphere filled with local events, festivals, and ample opportunities for water sports at nearby Lake Michigan.During these summer months, visitors can expect comfortable temperatures ranging from 20 to 30 degrees Celsius, great for exploring the scenic parks or enjoying a leisurely day at the beach. The long daylight hours allow for plenty of sightseeing, whether you're hiking the trails of the nearby Kettle Moraine State Forest or indulging in a picnic at one of the area's beautiful lakesides.For those looking for a more budget-friendly option, consider planning your visit in December. While this month marks the low season, it offers a unique charm with festive holiday decorations and local events that celebrate winter. Plus, travellers can enjoy a quieter experience, ideal for relaxing and unwinding.
What are the top attractions in Pleasant Prairie?
In Pleasant Prairie, visitors can enjoy a variety of attractions that cater to different interests. The Pleasant Prairie Premium Outlets offer a fantastic shopping experience with a range of brand-name stores and dining options, making it a popular destination for shoppers. For those seeking outdoor activities, the nearby Lake Andrea in Prairie Springs Park provides opportunities for fishing, kayaking, and walking trails, all set within a picturesque natural environment.Families can also visit the Jelly Belly Candy Company, where guided tours offer a sweet insight into the candy-making process, complete with samples to enjoy. Additionally, the area hosts several community events and festivals throughout the year, fostering a vibrant local culture.
Are all fees included in the Pleasant Prairie holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pleasant Prairie holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pleasant Prairie with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pleasant Prairie holiday homes?
You can find great discounts on holiday homes in Pleasant Prairie on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pleasant Prairie holiday home booking on Stayz?
To find Pleasant Prairie holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pleasant Prairie?
A long-stay holiday home in Pleasant Prairie is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pleasant Prairie holiday home?
Book your Pleasant Prairie holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pleasant Prairie?
Prices for holiday homes in Pleasant Prairie vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pleasant Prairie to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.